Heterocyclic Compounds as Pesticides

ABSTRACT

The present application relates to novel heterocyclic compounds, to the use thereof for controlling animal pests, which include arthropods and especially insects, and to processes for preparing the novel compounds.

The present application relates to novel heterocyclic compounds, toprocesses for preparation thereof and to the use thereof for controllinganimal pests, which include arthropods and especially insects, and alsoto intermediates for preparation of the heterocyclic compounds.

Particular thiazolyl, thiadiazolyl and pyrazolyl compounds have alreadybecome known as insecticidally active ingredients (cf. WO 2010/006713A2).

Modern crop protection compositions have to meet many demands, forexample in relation to the level, duration and breadth of their actionand possible use. Questions of toxicity and of combinability with otheractive ingredients or formulation auxiliaries play a role, as does thequestion of the expense that the synthesis of an active ingredientrequires. In addition, resistances can occur. For all these reasons, thesearch for novel crop protection compositions cannot be considered to becomplete, and there is a constant need for novel compounds havingproperties which, compared to the known compounds, are improved at leastin relation to individual aspects.

It was an object of the present invention to provide compounds whichwiden the spectrum of the pesticides in various respects.

This object, and further objects which are not stated explicitly but canbe discerned or derived from the connections discussed herein, areachieved by novel compounds of the formula (I)

in which

-   A¹ and A² are each independently hydrogen, halogen, cyano, nitro,    alkyl, cycloalkyl or alkoxy,-   G¹ is N or C-A¹ and-   G² is a radical from the group of

in which the arrow in each case marks the bond to the adjacent ring,

-   R¹ in the case of the heterocycles (A) and (D) is hydrogen, halogen,    cyano, alkyl, alkoxy, amino, alkylamino, dialkylamino, alkylthio or    haloalkyl and-   R¹ in the case of heterocycle (C) is hydrogen, alkyl or haloalkyl,-   B is hydrogen, halogen, cyano, nitro, alkyl, cycloalkyl, haloalkyl,    amino, alkylamino, dialkylamino, alkylthio or alkoxy and-   G³ is optionally substituted heterocyclyl, optionally substituted    heteroaryl or optionally substituted aryl and-   G⁴ is a radical from the group of

-   -   and in the case of the heterocycles (A), (B) and (C) is also the        radical

-   -   in which the arrow in each case marks the bond to G³,

-   X is oxygen or sulphur,

-   n is 1 or 2,

-   R² is a radical from the group of hydrogen, alkyl, haloalkyl,    cyanoalkyl, alkoxy, haloalkoxy, alkenyl, alkynyl and alkoxyalkyl, in    each case optionally halogen-substituted alkylcarbonyl and    alkylsulphonyl, in each case optionally halogen-substituted    alkoxycarbonyl, in each case optionally halogen-, alkyl-, alkoxy-,    haloalkyl- and cyano-substituted cycloalkylcarbonyl, or a cation,    for example a mono- or divalent metal ion or an optionally alkyl- or    arylalkyl-substituted ammonium ion,

-   R³ and R⁷ are each independently a radical from the group of in each    case optionally substituted alkyl, alkenyl and alkynyl, in each case    optionally substituted cycloalkyl, cycloalkylalkyl and cycloalkenyl,    in which the rings may contain at least one heteroatom from the    group of sulphur, oxygen (where oxygen atoms must not be immediately    adjacent) and nitrogen, in each case optionally substituted aryl,    heteroaryl, arylalkyl and heteroarylalkyl and an optionally    substituted amino group,

-   R² and R³ may also form, together with the N—S(O)_(n) group to which    they are bonded, a saturated or unsaturated and optionally    substituted 4- to 8-membered ring which may contain one or more    further heteroatoms from the group of sulphur, oxygen (where oxygen    atoms must not be immediately adjacent) and nitrogen and/or at least    one carbonyl group,

-   R⁵ is a radical from the group of in each case optionally    substituted alkyl, alkoxy, alkenyl and alkynyl, in each case    optionally substituted cycloalkyl, cycloalkylalkyl and cycloalkenyl,    in which the rings may contain at least one heteroatom from the    group of sulphur, oxygen (where oxygen atoms must not be immediately    adjacent) and nitrogen, in each case optionally substituted aryl,    heteroaryl, arylalkyl and heteroarylalkyl and an optionally    substituted amino group,

-   R⁸ is a radical from the group of hydrogen, in each case optionally    substituted alkyl, alkoxy, alkenyl and alkynyl, in each case    optionally substituted cycloalkyl, cycloalkylalkyl and cycloalkenyl,    in which the rings may contain at least one heteroatom from the    group of sulphur, oxygen (where oxygen atoms must not be immediately    adjacent) and nitrogen, in each case optionally substituted aryl,    heteroaryl, arylalkyl and heteroarylalkyl and an optionally    substituted amino group,

-   R² and R⁵ may also form, together with the N—C(X) group to which    they are bonded, a saturated or unsaturated and optionally    substituted 4- to 8-membered ring which may contain one or more    further heteroatoms from the group of sulphur, oxygen (where oxygen    atoms must not be immediately adjacent) and nitrogen and/or at least    one carbonyl group,

-   R⁶ is hydrogen or alkyl,

-   R² and R⁶ may also form, together with the nitrogen atoms to which    they are bonded, a saturated or unsaturated and optionally    substituted 4- to 8-membered ring which may contain at least one    further heteroatom from the group of sulphur, oxygen (where oxygen    atoms must not be immediately adjacent) and nitrogen and/or at least    one carbonyl group,

-   R² and R⁷ in the radical (E) may also form, together with the    N—S(O)_(n) group to which they are bonded, a saturated or    unsaturated and optionally substituted 4- to 8-membered ring which    may contain one or more further heteroatoms from the group of    sulphur, oxygen (where oxygen atoms must not be immediately    adjacent) and nitrogen and/or at least one carbonyl group,

-   R⁶ and R⁷ may also form, together with the N—S(O)_(n) group to which    they are bonded, a saturated or unsaturated and optionally    substituted 4- to 8-membered ring which may contain one or more    further heteroatoms from the group of sulphur, oxygen (where oxygen    atoms must not be immediately adjacent) and nitrogen and/or at least    one carbonyl group,

-   R² and R⁸ may also form, together with the nitrogen atom to which    they are bonded, a saturated or unsaturated and optionally    substituted 4- to 8-membered ring which may contain one or more    further heteroatoms from the group of sulphur, oxygen (where oxygen    atoms must not be immediately adjacent) and nitrogen and/or at least    one carbonyl group,

-   L is oxygen or sulphur,

-   R⁹ and R¹⁰ are each independently an in each case optionally    substituted radical from the group of alkyl, alkenyl, alkynyl,    alkoxy, alkenyloxy, alkynyloxy, cycloalkyl, cycloalkyloxy,    cycloalkenyloxy, cycloalkylalkoxy, alkylthio, alkenylthio, phenoxy,    phenylthio, benzyloxy, benzylthio, heteroaryloxy, heteroarylthio,    heteroarylalkoxy and heteroarylalkylthio,

-   R⁹ and R¹⁰ may also form, together with the phosphorus atom to which    they are bonded, a saturated or unsaturated and optionally    substituted 5- to 7-membered ring which may contain one or two    heteroatoms from the group of oxygen (where oxygen atoms must not be    immediately adjacent) and sulphur, and

-   R¹¹ and R¹² are each independently an in each case optionally    substituted radical from the group of alkyl, alkenyl, alkynyl,    phenyl and phenylalkyl,

-   Y¹ and Y² are each independently C═O or S(O)₂,

-   m is 1, 2, 3 or 4,

-   R¹³ is a radical from the group of hydrogen, alkyl, haloalkyl,    cyano, cyanoalkyl, hydroxyalkyl, hydroxyl, alkoxy, alkoxyalkyl,    alkylthioalkyl, alkenyl, haloalkenyl, cyanoalkenyl, alkynyl,    haloalkynyl, cyanoalkynyl, alkylcarbonyl and alkoxycarbonyl,

-   Y³ is a radical from the group of alkoxy, haloalkoxy, alkylthio,    haloalkylthio and NR¹⁴R¹⁵ where R¹⁴ and R¹⁵ are each independently    radicals from the group of hydrogen, alkyl, cycloalkyl,    cycloalkylalkyl, haloalkyl, cyano, cyanoalkyl, hydroxyl, alkoxy,    haloalkoxy, hydroxyalkyl, alkoxyalkyl, alkylthioalkyl, alkenyl,    haloalkenyl, cyanoalkenyl, alkynyl, haloalkynyl, cyanoalkynyl,    alkylcarbonyl and alkoxycarbonyl, or R¹⁴ and R¹⁵ together with the    nitrogen atom to which they are bonded may form an optionally    substituted saturated or unsaturated 5- to 8-membered ring    optionally containing heteroatoms,

-   G³ and G⁴ may additionally also together form an optionally    substituted heterocycle which optionally contains one or more    further heteroatoms from the group of oxygen, nitrogen and sulphur,    and salts and N-oxides of the compounds of the formula (I).

When G¹ is N, compounds of the formula (Ia) are thus obtained

and, when G¹ is C-A¹, compounds of the formula (Ib) are obtained

in which the remaining substituents are each as defined above.

It has additionally been found that the compounds of the formula (I) canbe obtained by the processes described below.

Depending on the G⁴ radical, the compounds of the formula (I) can bedivided into the substructures (I_(E)) to (I_(M)).

Compounds of the formula (I_(E-G), I_(M)) can be prepared, for example,by reacting the carboxylic acids of the formula (II₁) or the acidchlorides thereof with amine derivatives of the formula (III_(E-G),III_(M)).

where R^(13′) is

Compounds of the formula (I₁) can be prepared, for example, as will beexplained in detail later, from the amines of the formula (II₂).

Compounds of the formula (I_(J)) can be prepared, for example, byreacting the heterocyclic amines of the formula (II₂) with sulphonylchlorides of the formula (III_(J)).

Compounds of the formula (I_(K)) can be prepared, for example, byreacting sulphonyl chlorides of the formula (II₃) with amines of theformula (III_(K)).

Compounds of the formula (I_(L)) can be prepared, for example, byreacting sulphonyl chlorides of the formula (II₃) with amides of theformula (III_(L)).

Compounds of the formula (I_(N)) can be prepared, for example, byreacting nitriles of the formula (II₄) or thio amides of the formula(II₅) with oxy, thio or amino derivatives of the formula (III_(N)).

Finally, it has been found that novel compounds of the formula (I) havevery pronounced biological properties and are suitable in particular forcontrolling animal pests, especially insects, arachnids and nematodes,which are encountered in agriculture, in forests, in the protection ofstored products and materials and in the hygiene sector.

The compounds of the general formula (I) may, where appropriate,depending on the nature of the substituents, be in the form of geometricand/or optically active isomers or corresponding isomer mixtures indifferent compositions. The invention relates both to the pure isomersand to the isomer mixtures.

The inventive compounds may also be present as metal complexes, asdescribed for other amides, for example, in DE 2221647.

Preferred substituents or ranges for the radicals shown in the compoundsof the formula (I) are elucidated below.

-   A¹ and A² are each independently hydrogen, halogen, cyano, nitro,    C₁-C₆-alkyl, C₃-C₆-cycloalkyl or C₁-C₆-alkoxy.-   G¹ is N or C-A¹.-   G² is a radical from the group of

-   -   in which the arrow marks the bond to the adjacent ring.

-   R¹ in the case of the heterocycles (A) and (D) is hydrogen, halogen,    cyano, C₁-C₆-alkyl, C₁-C₆-alkoxy or C₁-C₆-haloalkyl.

-   R¹ in the case of heterocycle (C) is hydrogen, C₁-C₆-alkyl or    C₁-C₆-haloalkyl.

-   B is hydrogen, halogen, cyano, nitro, C₁-C₆-alkyl, C₁-C₆-haloalkyl,    C₁-C₆-alkoxy or C₃-C₆-cycloalkyl.

-   G³ is in each case optionally halogen-, cyano-, nitro-, amino-,    C₁-C₆-alkylamino-, di(C₁-C₆)-alkylamino-, C₁-C₆-alkyl-,    C₃-C₆-cycloalkyl-, C₁-C₆-haloalkyl-, hydroxyl-, C₁-C₆-alkoxy-,    C₁-C₆-haloalkoxy-, C₁-C₆-alkylthio-, C₁-C₆-alkylcarbonyl-,    C₁-C₆-alkoxycarbonyl-, C₂-C₆-alkenyl- or C₂-C₆-alkynyl-substituted    5-membered heteroaryl or 6-membered heteroaryl; G³ is especially in    each case optionally halogen-, cyano-, nitro-, amino-,    C₁-C₆-alkylamino-, di-(C₁-C₆)-alkylamino-, C₁-C₆-alkyl-,    C₃-C₆-cycloalkyl-, C₁-C₆-haloalkyl-, hydroxyl-, C₁-C₆-alkoxy-,    C₁-C₆-haloalkoxy-, C₁-C₆-alkylthio-, C₁-C₆-alkylcarbonyl-,    C₁-C₆-alkoxycarbonyl-, C₂-C₆-alkenyl- or C₂-C₆-alkynyl-substituted    pyrazolyl, oxazolyl, thiazolyl, oxadiazolyl, triazolyl, pyridinyl,    pyridazinyl, pyrimidinyl, pyrazinyl or triazinyl,    -   and additionally optionally halogen-, cyano-, nitro-, amino-,        C₁-C₆-alkylamino-, di(C₁-C₆)-alkylamino-, C₁-C₆-alkyl-,        C₃-C₆-cycloalkyl-, C₁-C₆-haloalkyl-, hydroxyl-, C₁-C₆-alkoxy-,        C₁-C₆-haloalkoxy-, C₁-C₆-alkylthio-, C₁-C₆-alkylcarbonyl-,        C₁-C₆-alkoxycarbonyl-, C₂-C₆-alkenyl- or        C₂-C₆-alkynyl-substituted phenyl,    -   and when G⁴ is one of the radicals (E), (F), (G), (H), (K), (L)        and (M),

-   G³ may also be optionally halogen-, cyano-, nitro-, amino-,    C₁-C₆-alkylamino-, di(C₁-C₆)-alkylamino-, C₁-C₆-alkyl-,    C₃-C₆-cycloalkyl-, C₁-C₆-haloalkyl-, hydroxyl-, C₁-C₆-alkoxy-,    C₁-C₆-haloalkoxy-, C₁-C₆-alkylthio-, C₁-C₆-alkylcarbonyl-,    C₁-C₆-alkoxycarbonyl-, C₂-C₆-alkenyl- or C₂-C₆-alkynyl-substituted    5-membered heterocyclyl or 6-membered heterocyclyl; G³ in that case    is especially a radical from the group of

-   -   in which the arrow in each case marks the bond to G², and G¹ is        also shown for illustration.

-   G⁴ is a radical from the group of

-   -   and in the case of the heterocycles (A), (B) and (C) is also the        radical

-   -   in which the arrow marks the bond to G³.

-   X is oxygen or sulphur.

-   n is 1 or 2.

-   R² is a radical from the group of hydrogen, C₁-C₆-alkyl,    C₁-C₆-haloalkyl, cyano-C₁-C₆-alkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy,    C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₁-C₆-alkoxy-C₁-C₆-alkyl, in each case    optionally halogen-substituted C₁-C₆-alkylcarbonyl and    C₁-C₆-alkylsulphonyl, optionally halogen-substituted    C₁-C₆-alkoxycarbonyl, optionally halogen-, C₁-C₆-alkyl-,    C₁-C₆-alkoxy-, C₁-C₆-haloalkyl- and cyano-substituted    C₃-C₆-cycloalkylcarbonyl, or a cation, for example a mono- or    divalent metal ion, such as Na⁺ and K⁺, or an optionally    C₁-C₆-alkyl- or aryl-C₁-C₆-alkyl-substituted ammonium ion.

-   R³ and R⁷ are each independently a radical from the group of in each    case optionally halogen-, C₁-C₆-alkoxy-, C₁-C₆-haloalkoxy-,    C₁-C₆-alkylthio-, C₁-C₆-haloalkylthio-, C₁-C₆-alkylsulphinyl-,    C₁-C₆-haloalkylsulphinyl-, C₁-C₆-alkylsulphonyl- and    C₁-C₆-haloalkylsulphonyl-substituted C₁-C₆-alkyl, C₂-C₆-alkenyl and    C₁-C₆-alkynyl, in each case optionally halogen-, C₁-C₆-alkyl-,    C₁-C₆-haloalkyl-, C₁-C₆-alkoxy- or C₁-C₆-haloalkoxy-substituted    C₁-C₆-cycloalkyl, C₃-C₆-cycloalkyl-C₁-C₆-alkyl and    C₃-C₆-cycloalkenyl, in which the rings may contain at least one    heteroatom from the group of sulphur, oxygen (where oxygen atoms    must not be immediately adjacent)    -   and nitrogen (and especially

-   -   where the arrow in each case marks the bond to the sulphur atom        in the radicals (E), (F) and (J)), in each case optionally        halogen-, cyano- (including in the alkyl moiety), nitro-,        C₁-C₆-alkyl-, C₁-C₆-haloalkyl-, C₃-C₆-cycloalkyl-,        C₁-C₆-alkoxy-, C₁-C₆-haloalkoxy-, C₁-C₆ alkylthio-,        C₁-C₆-haloalkylthio-, C₁-C₆-alkylsulphinyl-,        C₁-C₆-haloalkylsulphinyl-, C₁-C₆-alkylsulphonyl-,        C₁-C₆-haloalkylsulphonyl-, amino-, C₁-C₆-alkylamino-,        di(C₁-C₆-alkyl)amino-, C₁-C₆-alkylcarbonylamino-,        C₁-C₆-alkoxycarbonylamino-, C₁-C₆-alkoxy-C₁-C₆-alkyl-,        C₁-C₆-haloalkoxy-C₁-C₆-alkyl-, C₂-C₆-alkenyl-, C₂-C₆-alkynyl-,        C₃-C₆-cycloalkyl-C₁-C₆-alkyl-, C₁-C₆-alkylcarbonyl-,        C₁-C₆-alkoxycarbonyl- or aminocarbonyl-substituted aryl,        heteroaryl, aryl-C₁-C₆-alkyl and heteroaryl-C₁-C₆-alkyl, or        NR′R″ in which R′ and R″ are each independently a radical from        the group of hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl,        C₃-C₆-cycloalkyl, C₃-C₆-cycloalkyl-C₁-C₆-alkyl, C₁-C₆-alkoxy,        C₁-C₆-alkylcarbonyl and C₁-C₆-alkoxylcarbonyl.

-   R² and R³ may also, together with the N—S(O)_(n) group to which they    are bonded, form a saturated or unsaturated and optionally halogen-,    C₁-C₆-alkyl-, C₁-C₆-haloalkyl-, C₁-C₆-alkoxy-,    C₁-C₆-haloalkoxy-substituted 5- to 7-membered ring which may contain    one or more further heteroatoms from the group of sulphur, oxygen    (where oxygen atoms must not be immediately adjacent) and nitrogen    and/or at least one carbonyl group; R² and R³ may especially,    together with the N—S(O)_(n) group to which they are bonded, be a    radical from the group of

-   -   (in which the arrow again in each case marks the bond to G³).

-   R⁵ is a radical from the group of in each case optionally halogen-,    C₁-C₆-alkoxy-, C₁-C₆-haloalkoxy-, C₁-C₆-alkylthio-,    C₁-C₆-haloalkylthio-, C₁-C₆-alkylsulphinyl-,    C₁-C₆-haloalkylsulphinyl-, C₁-C₆-alkylsulphonyl- or    C₁-C₆-haloalkylsulphonyl-substituted C₁-C₆-alkyl, C₁-C₆-alkoxy,    C₂-C₆-alkenyl and C₂-C₆-alkynyl, in each case optionally halogen-,    C₁-C₆-alkyl-, C₁-C₆-haloalkyl-, C₁-C₆-alkoxy- or    C₁-C₆-haloalkoxy-substituted C₃-C₆-cycloalkyl,    C₃-C₆-cycloalkyl-C₁-C₆-alkyl and C₃-C₆-cycloalkenyl, in which the    rings may contain at least one heteroatom from the group of sulphur,    oxygen (where oxygen atoms must not be immediately adjacent) and    nitrogen, in each case optionally halogen-, cyano-(including in the    alkyl moiety), nitro-, C₁-C₆-alkyl-, C₁-C₆-haloalkyl-,    C₃-C₆-cycloalkyl-, C₁-C₆-alkoxy-, C₁-C₆-haloalkoxy-,    C₁-C₆-alkylthio-, C₁-C₆-haloalkylthio-, C₁-C₆-alkylsulphinyl-,    C₁-C₆-haloalkylsulphinyl-, C₁-C₆-alkylsulphonyl-,    C₁-C₆-haloalkylsulphonyl-, amino-, C₁-C₆-alkylamino-,    di(C₁-C₆-alkyl)amino-, C₁-C₆-alkylcarbonylamino-,    C₁-C₆-alkoxycarbonylamino-, C₁-C₆-alkoxy-C₁-C₆-alkyl-,    C₁-C₆-haloalkoxy-C₁-C₆-alkyl-, C₂-C₆-alkenyl-, C₂-C₆-alkynyl-,    C₃-C₆-cycloalkyl-C₁-C₆-alkyl-, C₁-C₆-alkylcarbonyl-,    C₁-C₆-alkoxycarbonyl- or aminocarbonyl-substituted aryl, heteroaryl,    aryl-C₁-C₆-alkyl and heteroaryl-C₁-C₆-alkyl, or NR′R″ in which R′    and R″ are each independently a radical from the group of hydrogen,    C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₃-C₆-cycloalkyl, C₁-C₆-alkoxy,    C₁-C₆-alkylcarbonyl and C₁-C₆-alkoxylcarbonyl.

-   R⁸ is a radical from the group of hydrogen, in each case optionally    halogen-, C₁-C₆-alkoxy-, C₁-C₆-haloalkoxy-, C₁-C₆-alkylthio-,    C₁-C₆-haloalkylthio-, C₁-C₆-alkylsulphinyl-,    C₁-C₆-haloalkylsulphinyl-, C₁-C₆-alkylsulphonyl- or    C₁-C₆-haloalkylsulphonyl-substituted C₁-C₆-alkyl, C₁-C₆-alkoxy,    C₂-C₆-alkenyl and C₂-C₆-alkynyl, in each case optionally halogen-,    C₁-C₆-alkyl-, C₁-C₆-haloalkyl-, C₁-C₆-alkoxy- or    C₁-C₆-haloalkoxy-substituted C₃-C₆-cycloalkyl,    C₃-C₆-cycloalkyl-C₁-C₆-alkyl and C₃-C₆-cycloalkenyl, in which the    rings may contain at least one heteroatom from the group of sulphur,    oxygen (where oxygen atoms must not be immediately adjacent) and    nitrogen, in each case optionally halogen-, cyano-(including in the    alkyl moiety), nitro-, C₁-C₆-alkyl-, C₁-C₆-haloalkyl-,    C₃-C₆-cycloalkyl-, C₁-C₆-alkoxy-, C₁-C₆-haloalkoxy-,    C₁-C₆-alkylthio-, C₁-C₆-haloalkylthio-, C₁-C₆-alkylsulphinyl-,    C₁-C₆-haloalkylsulphinyl-, C₁-C₆-alkylsulphonyl-,    C₁-C₆-haloalkylsulphonyl-, amino-, C₁-C₆-alkylamino-,    di(C₁-C₆-alkyl)amino-, C₁-C₆-alkylcarbonylamino-,    C₁-C₆-alkoxycarbonylamino-, C₁-C₆-alkoxy-C₁-C₆-alkyl-, C₁-C₆    haloalkoxy-C₁-C₆-alkyl-, C₂-C₆-alkenyl-, C₂-C₆-alkynyl-,    C₃-C₆-cycloalkyl-C₁-C₆-alkyl-, C₁-C₆-alkylcarbonyl-,    C₁-C₆-alkoxycarbonyl- or aminocarbonyl-substituted aryl heteroaryl,    aryl-C₁-C₆-alkyl and heteroaryl-C₁-C₆-alkyl, or NR′R″ in which R′    and R″ are each independently a radical from the group of hydrogen,    C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₃-C₆-cycloalkyl, C₁-C₆-alkoxy,    C₁-C₆-alkylcarbonyl and C₁-C₆-alkoxylcarbonyl.

-   R² and R⁵ may also, together with the N—C(X) group to which they are    bonded, form a saturated or unsaturated and optionally halogen-,    C₁-C₆-alkyl-, C₁-C₆-haloalkyl-, C₁-C₆-alkoxy-,    C₁-C₆-haloalkoxy-substituted 5- to 7-membered ring which may contain    one or more further heteroatoms from the group of sulphur, oxygen    (where oxygen atoms must not be immediately adjacent) and nitrogen    and/or at least one carbonyl group; R² and R⁵ may especially,    together with the N—C(X) group to which they are bonded, be a    radical from the group of

-   -   (in which the arrow in each case marks the bond to the sulphur        atom in the radical (L)).

-   R⁶ is hydrogen or C₁-C₆-alkyl.

-   R² and R⁶ may also, together with the nitrogen atoms to which they    are bonded, be a saturated or unsaturated and optionally halogen-,    C₁-C₆-alkyl-, C₁-C₆-haloalkyl-, C₁-C₆-alkoxy-,    C₁-C₆-haloalkoxy-substituted 5- to 7-membered ring which may contain    at least one further heteroatom from the group of sulphur, oxygen    (where oxygen atoms must not be immediately adjacent) and nitrogen    and/or at least one carbonyl group; R² and R⁶ may especially,    together with the N—N group to which they are bonded, be a radical    from the group of

(where the whole radical (F) is depicted and the arrow again in eachcase marks the bond to G³).

-   R² and R⁷ may also, in the case that G³ is (E), together with the    N—S(O)_(n) group to which they are bonded, form a saturated or    unsaturated and optionally halogen-, C₁-C₆-alkyl-, C₁-C₆-haloalkyl-,    C₁-C₆-alkoxy-, C₁-C₆-haloalkoxy-substituted 5- to 7-membered ring    which may contain one or more further heteroatoms from the group of    sulphur, oxygen (where oxygen atoms must not be immediately    adjacent) and nitrogen and/or at least one carbonyl group; R² and R⁷    may especially, together with the N—S(O)_(n) group to which they are    bonded, be a radical from the group of

(in which the arrow in each case marks the bond to the C(X) group).

-   R⁶ and R⁷ may also, in the case that G³ is (F), together with the    N—S(O)_(n) group to which they are bonded, form a saturated or    unsaturated and optionally halogen-, C₁-C₆-alkyl-, C₁-C₆-haloalkyl-,    C₁-C₆-alkoxy-, C₁-C₆-haloalkoxy-substituted 5- to 7-membered ring    which may contain one or more further heteroatoms from the group of    sulphur, oxygen (where oxygen atoms must not be immediately    adjacent) and nitrogen and/or at least one carbonyl group; R⁶ and R⁷    may especially, together with the N—S(O)_(n) group to which they are    bonded, be a radical from the group of

(in which the N—R² group is also shown and the arrow in each case marksthe bond to the C(X) group).

-   R² and R⁸ may also, together with the nitrogen atom to which they    are bonded, form a saturated or unsaturated and optionally halogen-,    C₁-C₆-alkyl-, C₁-C₆-haloalkyl-, C₁-C₆-alkoxy-,    C₁-C₆-haloalkoxy-substituted 5- to 7-membered ring which may contain    one or more further heteroatoms from the group of sulphur, oxygen    (where oxygen atoms must not be immediately adjacent) and nitrogen    and/or at least one carbonyl group; R² and R⁸ may especially,    together with the nitrogen atom to which they are bonded, be a    radical from the group of

-   -   (in which the arrow in each case marks the bond to the sulphur        atom in the radical (K)).

-   L is oxygen or sulphur.

-   R⁹ and R¹⁰ are each independently an in each case optionally    halogen-substituted radical from the group of C₁-C₆-alkyl,    C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₁-C₆-alkoxy, C₁-C₆-alkenyloxy,    C₂-C₆-alkynyloxy, C₃-C₆-cycloalkyl, C₃-C₆-cycloalkyloxy,    C₁-C₆-cycloalkenyloxy, C₃-C₆-cycloalkyl-C₁-C₆-alkoxy,    C₁-C₆-alkylthio, C₂-C₆-alkenylthio, phenoxy, phenylthio, benzyloxy,    benzylthio, heteroaryloxy, heteroarylthio, heteroaryl-C₁-C₆-alkoxy    and heteroaryl-C₁-C₆-alkylthio.

-   R⁹ and R¹⁰ may also, together with the phosphorus atom to which they    are bonded, form a saturated or unsaturated and optionally halogen-,    C₁-C₆-alkyl-, C₁-C₆-haloalkyl-, C₁-C₆-alkoxy-,    C₁-C₆-haloalkoxy-substituted 5- to 7-membered ring which may contain    one or two heteroatoms from the group of oxygen (where oxygen atoms    must not be immediately adjacent) and sulphur, R⁹ and R¹⁰ may    especially, together with the phosphorus atom to which they are    bonded, be the radical

-   -   (in which the arrow marks the bond to the nitrogen atom in the        radical (G)).

-   R¹¹ and R¹² are each independently an in each case optionally    halogen-, C₁-C₆-alkyl-, C₁-C₆-haloalkyl-, C₁-C₆-alkoxy-,    C₁-C₆-haloalkoxy-substituted radical from the group of C₁-C₆-alkyl,    C₂-C₆-alkenyl, C₂-C₆-alkynyl, phenyl and phenyl-C₁-C₆-alkyl.

-   Y¹ and Y² are each independently C═O or S(O)₂.

-   m is 1, 2, 3 or 4.

-   R¹³ is a radical from the group of hydrogen, C₁-C₆-alkyl,    C₁-C₆-haloalkyl, cyano, C₁-C₆-cyanoalkyl, C₁-C₆-hydroxyalkyl,    hydroxyl, C₁-C₆-alkoxy, C₁-C₆-alkoxy-C₁-C₆-alkyl,    C₁-C₆-alkylthio-C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-haloalkenyl,    C₁-C₆-cyanoalkenyl, C₁-C₆-alkynyl, C₂-C₆-haloalkynyl,    C₂-C₆-cyanoalkynyl, C₁-C₇-alkylcarbonyl and C₁-C₇-alkoxycarbonyl.

-   Y³ is a radical from the group of C₁-C₆-alkoxy, C₁-C₆-haloalkoxy,    C₁-C₆-alkylthio, C₁-C₆-haloalkylthio and NR¹⁴R¹⁵ where R¹⁴ and R¹⁵    are each independently a radical from the group of hydrogen,    C₁-C₆-alkyl, C₃-C₈-cycloalkyl, C₃-C₈-cycloalkyl-C₁-C₆-alkyl,    C₁-C₆-haloalkyl, cyano, C₁-C₆-cyanoalkyl, hydroxyl, C₁-C₆-alkoxy,    C₁-C₆-haloalkoxy, C₁-C₆-hydroxyalkyl, C₁-C₆-alkoxy-C₁-C₆-alkyl,    C₁-C₆-alkylthio-C₁-C₆-alkyl, C₁-C₆-alkenyl, C₁-C₆-haloalkenyl,    C₂-C₆-cyanoalkenyl, C₂-C₆-alkynyl, C₂-C₆-haloalkynyl,    C₂-C₆-cyanoalkynyl, C₁-C₇-alkylcarbonyl and C₁-C₇-alkoxycarbonyl, or    R¹⁴ and R¹⁵ together with the nitrogen atom to which they are bonded    are an optionally halogen-, cyano-, C₁-C₆-alkyl-, C₁-C₆-haloalkyl-,    C₁-C₆-alkoxy-, C₃-C₈-cycloalkyl- or C₁-C₆-alkylthio-substituted    saturated or unsaturated 5- to 8-membered ring which may contain one    or more further atoms from the group of sulphur, oxygen (where    oxygen atoms must not be immediately adjacent) and nitrogen and/or    at least one carbonyl group; R¹⁴ and R¹⁵ may especially, together    with the nitrogen atom to which they are bonded, be a radical from    the group of

-   -   (in which the arrow in each case marks the bonds to the carbon        atom in the (N) radical).

-   G³ and G⁴ may additionally together form an optionally substituted    heterocycle which optionally contains further heteroatoms from the    group of oxygen, nitrogen and sulphur; G³ and G⁴ may especially form    a bicycle from the group of

-   -   (in which the arrow marks the bond to G²).

Particularly preferred substituents or ranges for the radicals shown inthe compounds of the formula (I) are elucidated below.

-   A¹ is hydrogen, halogen or cyano, and A¹ is especially a radical    from the group of hydrogen, fluorine and chlorine.-   A² is hydrogen.-   G¹ is N or C-A¹.-   G² is a radical from the group of

-   -   in which the arrow marks the bond to the adjacent ring.

-   R¹ is hydrogen or C₁-C₄-alkyl, and R¹ is especially hydrogen or    methyl.

-   B is hydrogen.

-   G³ is in each case optionally halogen-, cyano-, nitro-, amino-,    C₁-C₆-alkylamino-, di-C₁-C₆-alkylamino-, C₁-C₆-alkyl-,    C₃-C₆-cycloalkyl-, C₁-C₆-haloalkyl-, hydroxyl-, C₁-C₆-alkoxy-,    C₁-C₆-haloalkoxy-, C₁-C₆-alkylthio-, C₁-C₆-alkylcarbonyl-,    C₁-C₆-alkoxycarbonyl-, C₂-C₆-alkenyl- or C₂-C₆-alkynyl-substituted    5-membered heteroaryl or 6-membered heteroaryl; G³ is especially    optionally halogen-, cyano-, nitro-, amino-, C₁-C₆-alkylamino-,    di-C₁-C₆-alkylamino-, C₁-C₆-alkyl-, C₃-C₆-cycloalkyl-,    C₁-C₆-haloalkyl-, hydroxyl-, C₁-C₆-alkoxy-, C₁-C₆-haloalkoxy-,    C₁-C₆-alkylthio-, C₁-C₆-alkylcarbonyl-, C₁-C₆-alkoxycarbonyl-,    C₂-C₆-alkenyl- or C₂-C₆-alkynyl-substituted pyrazolyl, oxazolyl,    thiazolyl, oxadiazolyl, triazolyl, pyridinyl, pyridazinyl,    pyrimidinyl, pyrazinyl or triazinyl; G³ is with emphasis an    optionally halogen-, cyano-, methyl-, methoxy-, trifluoromethyl-,    amino- or dimethylamino-substituted radical from the group of

-   -   in which the arrow in each case marks the bond to G², and G⁴ is        also shown for illustration,        and additionally optionally halogen-, cyano-, nitro-, amino-,        C₁-C₆-alkylamino-, di-(C₁-C₆)-alkylamino-, C₁-C₆-alkyl-,        C₃-C₆-cycloalkyl-, C₁-C₆-haloalkyl-, hydroxyl-, C₁-C₆-alkoxy-,        C₁-C₆-haloalkoxy-, C₁-C₆-alkylthio-, C₁-C₆-alkylcarbonyl-,        C₁-C₆-alkoxycarbonyl-, C₂-C₆-alkenyl- or        C₂-C₆-alkynyl-substituted phenyl,        and when G⁴ is one of the radicals (E) and (L),

-   G³ may also be optionally halogen-, cyano-, nitro-, amino-,    C₁-C₆-alkylamino-, di(C₁-C₆)-alkylamino-, C₁-C₆-alkyl-,    C₃-C₆-cycloalkyl-, C₁-C₆-haloalkyl-, C₁-C₆-alkoxy-,    C₁-C₆-haloalkoxy-, C₁-C₆-alkylthio-, C₁-C₆-alkylcarbonyl-,    C₁-C₆-alkoxycarbonyl-, C₂-C₆-alkenyl- or C₂-C₆-alkynyl-substituted    5-membered heterocyclyl or 6-membered heterocyclyl from the group of

-   -   in which the arrow in each case marks the bond to G², and G⁴ is        also shown for illustration.

-   G⁴ is a radical from the group of

-   -   and in the case of the heterocycles (A), (B), and (C) is also        the radical

-   -   in which the arrow in each case marks the bond to G³.

-   X is oxygen.

-   n is 2.

-   R² is a radical from the group of hydrogen, C₁-C₄-alkyl,    C₂-C₄-alkynyl, cyano-C₁-C₄-alkyl and C₁-C₄-alkoxy-C₁-C₄-alkyl,    optionally halogen-substituted C₁-C₄-alkylcarbonyl or C₁-C₄    alkylsulphonyl, optionally halogen-substituted C₁-C₄-alkoxycarbonyl,    optionally halogen-, C₁-C₄-alkyl-, C₁-C₄-alkoxy-, C₁-C₄-haloalkyl-    and cyano-substituted C₃-C₆-cycloalkylcarbonyl, or a cation, for    example a mono- or divalent metal ion or an optionally C₁-C₄-alkyl-    or aryl-C₁-C₄-alkyl-substituted ammonium ion; R² is especially a    radical from the group of hydrogen, methyl, ethyl, CH₂OCH₃,    CH₂OCH₂CH₃, COCH₃, COCH₂CH₃, cyclopropyl, Na⁺, K⁺ and ⁺N(CH₃)₄.

-   R⁵ is a radical from the group of in each case optionally halogen-,    C₁-C₄-alkoxy-, C₁-C₄-haloalkoxy-, C₁-C₄-alkylthio-,    C₁-C₄-haloalkylthio-, C₁-C₄-alkylsulphinyl-,    C₁-C₄-haloalkylsulphinyl-, C₁-C₄-alkylsulphonyl- and    C₁-C₄-haloalkylsulphonyl-substituted C₁-C₄-alkyl, C₂-C₄-alkenyl and    C₂-C₄-alkynyl, in each case optionally halogen-, C₁-C₄-alkyl-,    C₁-C₄-haloalkyl-, C₁-C₄-alkoxy-, C₁-C₄-haloalkoxy-substituted    C₃-C₆-cycloalkyl, C₃-C₆-cycloalkyl-C₁-C₄-alkyl and    C₃-C₄-cycloalkenyl, in which the rings may contain at least one    heteroatom from the group of sulphur, oxygen (where oxygen atoms    must not be immediately adjacent) and nitrogen (and especially

-   -   where the arrow in each case marks the bond to the carbon atom        in the radical (L)), in each case optionally halogen-, cyano-        (including in the alkyl moiety), nitro-, C₁-C₄-alkyl-,        C₁-C₄-haloalkyl-, C₃-C₆-cycloalkyl-, C₁-C₄-alkoxy-,        C₁-C₄-haloalkoxy-, C₁-C₄-alkylthio-, C₁-C₄-haloalkylthio-,        C₁-C₄-alkylsulphinyl-, C₁-C₄-haloalkylsulphinyl-,        C₁-C₄-alkylsulphonyl-, C₁-C₄-haloalkylsulphonyl-, amino-,        C₁-C₄-alkylamino-, di(C₁-C₄-alkyl)amino-,        C₁-C₄-alkylcarbonylamino-, C₁-C₄-alkoxycarbonylamino-,        C₁-C₄-alkoxy-C₁-C₄-alkyl-, C₁-C₄-haloalkoxy-C₁-C₄-alkyl-,        C₂-C₄-alkenyl-, C₂-C₄-alkynyl-, C₃-C₆-cycloalkyl-C₁-C₄-alkyl-,        C₁-C₄-alkylcarbonyl-, C₁-C₄-alkoxycarbonyl- or        aminocarbonyl-substituted aryl, heteroaryl, aryl-C₁-C₄-alkyl and        heteroaryl-C₁-C₄-alkyl, or NR′R″ in which R′ and R″ are each        independently a radical from the group of hydrogen and        C₁-C₄-alkyl, and R⁵ is especially a radical from the group of        methyl, ethyl, i-propyl, CF₃, CHF₂, CH₂F, CH₂CF₃, cyclopropyl,        dimethylamino, diethylamino, phenyl and benzyl.

-   R⁷ is a radical from the group of in each case optionally halogen-,    C₁-C₄-alkoxy-, C₁-C₄-haloalkoxy-, C₁-C₄-alkylthio-,    C₁-C₄-haloalkylthio-, C₁-C₄-alkylsulphinyl-,    C₁-C₄-haloalkylsulphinyl-, C₁-C₄-alkylsulphonyl- and    C₁-C₄-haloalkylsulphonyl-substituted C₁-C₄-alkyl, C₂-C₄-alkenyl and    C₁-C₄-alkynyl, in each case optionally halogen-, C₁-C₄-alkyl-,    C₁-C₄-haloalkyl-, C₁-C₄-alkoxy-, C₁-C₄-haloalkoxy-substituted    C₃-C₆-cycloalkyl, C₃-C₆-cycloalkyl-C₁-C₄-alkyl and    C₃-C₄-cycloalkenyl, in which the rings may contain at least one    heteroatom from the group of sulphur, oxygen (where oxygen atoms    must not be immediately adjacent) and nitrogen (and especially

-   -   where the arrow in each case marks the bond to the sulphur atom        in the radical (E)), in each case optionally halogen-, cyano-        (including in the alkyl moiety), nitro-, C₁-C₄-alkyl-,        C₁-C₄-haloalkyl-, C₃-C₆-cycloalkyl-, C₁-C₄-alkoxy-,        C₁-C₄-haloalkoxy-, C₁-C₄-alkylthio-, C₁-C₄-haloalkylthio-,        C₁-C₄-alkylsulphinyl-, C₁-C₄-haloalkylsulphinyl-,        C₁-C₄-alkylsulphonyl-, C₁-C₄-haloalkylsulphonyl-, amino-,        C₁-C₄-alkylamino-, di(C₁-C₄-alkyl)amino-,        C₁-C₄-alkylcarbonylamino-, C₁-C₄-alkoxycarbonylamino-,        C₁-C₄-alkoxy-C₁-C₄-alkyl-, C₁-C₄-haloalkoxy-C₁-C₄-alkyl-,        C₁-C₄-alkenyl-, C₂-C₄-alkynyl-, C₃-C₆-cycloalkyl-C₁-C₄-alkyl-,        C₁-C₄-alkylcarbonyl-, C₁-C₄-alkoxycarbonyl- or        aminocarbonyl-substituted aryl, heteroaryl, aryl-C₁-C₄-alkyl and        heteroaryl-C₁-C₄-alkyl or NR′R″ in which R′ and R″ are each        independently a radical from the group of hydrogen, C₁-C₄-alkyl        and C₃-C₆-cycloalkyl-C₁-C₄-alkyl, and R⁷ is especially a radical        from the group of methyl, ethyl, i-propyl, CF₃, CHF₂, CH₂F,        CH₂CF₃, cyclopropyl, cyclopropylmethyl, cyclopropylethyl,        dimethylamino, diethylamino, phenyl and benzyl.

-   G³ and G⁴ may additionally also form an optionally substituted    heterocycle which optionally contains further heteroatoms from the    group of oxygen, nitrogen and sulphur, G³ and G⁴ may especially form    a bicycle from the group of

-   -   (in which the arrow marks the bond to G²).

-   R¹³ is a radical from the group of hydrogen, C₁-C₄-alkyl,    C₁-C₄-haloalkyl, cyano, C₁-C₄-cyanoalkyl, C₁-C₄-hydroxyalkyl,    hydroxyl, C₁-C₄-alkoxy, C₁-C₄-alkoxy-C₁-C₄-alkyl,    C₁-C₄-alkylthio-C₁-C₄-alkyl, C₁-C₄-alkenyl, C₁-C₄-haloalkenyl,    C₁-C₄-cyanoalkenyl, C₁-C₄-alkynyl, C₂-C₄-haloalkynyl,    C₂-C₄-cyanoalkynyl, C₁-C₅-alkylcarbonyl and C₁-C₅-alkoxycarbonyl.

-   Y³ is a radical from the group of C₁-C₄-alkoxy, C₁-C₄-haloalkoxy,    C₁-C₄-alkylthio, C₁-C₄-haloalkylthio and NR¹⁴R¹⁵ where R¹⁴ and R¹⁵    are each independently a radical from the group of hydrogen,    C₁-C₄-alkyl, C₃-C₆-cycloalkyl, C₃-C₆-cycloalkyl-C₁-C₄-alkyl,    C₁-C₄-haloalkyl, cyano, C₁-C₄-cyanoalkyl, hydroxyl, C₁-C₄-alkoxy,    C₁-C₄-haloalkoxy, C₁-C₄-hydroxyalkyl, C₁-C₄-alkoxy-C₁-C₄-alkyl,    C₁-C₄-alkylthio-C₁-C₄-alkyl, C₂-C₄-alkenyl, C₁-C₄-haloalkenyl,    C₂-C₄-cyanoalkenyl, C₂-C₄-alkynyl, C₂-C₄-haloalkynyl,    C₂-C₄-cyanoalkynyl, C₁-C₅-alkylcarbonyl, C₁-C₅-alkoxycarbonyl, or    R¹⁴ and R¹⁵ together with the nitrogen atom to which they are bonded    are an optionally halogen-, cyano-, C₁-C₄-alkyl-, C₁-C₄-haloalkyl-,    C₁-C₄-alkoxy, C₃-C₆-cycloalkyl- or C₁-C₄-alkylthio-substituted    saturated or unsaturated five- to eight-membered ring which may    contain a further atom from the group of sulphur, oxygen and    nitrogen and/or one carbonyl group; R¹⁴ and R¹⁵ may especially,    together with the nitrogen atom to which they are bonded, be a    radical from the group of

-   -   (in which the arrow in each case marks the bonds to the carbon        atom in the (N) radical).

Very particularly preferred substituents or ranges of the radicals shownin the compounds of the formula (I) are elucidated hereinafter.

-   A¹ is a radical from the group of hydrogen, fluorine and chlorine.-   A² is hydrogen.-   G¹ is N or C-A¹, which leads to compounds containing the following    structural elements:

in which the broken line means the bond to G²,

-   G² is a radical from the group of

-   -   in which the arrow in each case marks the bond to the adjacent        ring.

-   R¹ is hydrogen or methyl.

-   B is hydrogen.

-   G³ is an optionally halogen-, cyano-, methyl-, methoxy-,    trifluoromethyl-, amino- or dimethylamino-substituted radical from    the group of

-   -   in which the arrow in each case marks the bond to G², and G⁴ is        also shown for illustration.

-   G⁴ is a radical from the group of

-   -   and in the case of the heterocycles (A) and (B) is also the        radical

-   -   in which the arrow in each case marks the bond to G³.

-   X is oxygen.

-   n is 2.

-   R² is a radical from the group of hydrogen, C₁-C₄-alkyl,    C₁-C₄-alkynyl, cyano-C₁-C₄-alkyl and C₁-C₄-alkoxy-C₁-C₄-alkyl,    optionally halogen-substituted C₁-C₄-alkylcarbonyl or    C₁-C₄-alkylsulfonyl, optionally halogen-substituted    C₁-C₄-alkoxycarbonyl, optionally halogen-, C₁-C₄-alkyl-,    C₁-C₄-alkoxy-, C₁-C₄-halogenalkyl- and cyano-substituted    C₃-C₆-cycloalkylcarbonyl, or a cation, for example a mono- or    divalent metal ion or an optionally C₁-C₄-alkyl- or    aryl-C₁-C₄-alkyl-substituted ammonium ion; R² is especially a    radical from the group of hydrogen, methyl, ethyl, CH₂OCH₃,    CH₂OCH₂CH₃, COCH₃, COCH₂CH₃, CH₂CN, propynyl, cyclopropyl, Na⁺, K⁺    and ⁺N(CH₃)₄.

-   R⁵ is a radical from the group of in each case optionally halogen-,    C₁-C₄-alkoxy-, C₁-C₄-haloalkoxy-, C₁-C₄-alkylthio-,    C₁-C₄-haloalkylthio-, C₁-C₄-alkylsulphinyl-,    C₁-C₄-haloalkylsulphinyl-, C₁-C₄-alkylsulphonyl- and    C₁-C₄-haloalkylsulphonyl-substituted C₁-C₄-alkyl, C₂-C₄-alkenyl and    C₂-C₄-alkynyl, in each case optionally halogen-, C₁-C₄-alkyl,    C₁-C₄-haloalkyl-, C₁-C₄-alkoxy-, C₁-C₄-haloalkoxy-substituted    C₃-C₆-cycloalkyl, C₃-C₆-cycloalkyl-C₁-C₄-alkyl and    C₃-C₄-cycloalkenyl, in which the rings may contain at least one    heteroatom from the group of sulphur, oxygen (where oxygen atoms    must not be immediately adjacent) and nitrogen (and is especially

-   -   where the arrow in each case marks the bond to the carbon atom        in the (L) radical), in each case optionally halogen-, cyano-        (including in the alkyl moiety), nitro-, C₁-C₄-alkyl-,        C₁-C₄-haloalkyl-, C₃-C₆-cycloalkyl-, C₁-C₄-alkoxy-,        C₁-C₄-haloalkoxy-, C₁-C₄-alkylthio-, C₁-C₄-haloalkylthio-,        C₁-C₄-alkylsulphinyl-, C₁-C₄-haloalkylsulphinyl-,        C₁-C₄-alkylsulphonyl-, C₁-C₄-haloalkylsulphonyl-, amino-,        C₁-C₄-alkylamino-, di(C₁-C₄-alkyl)amino-,        C₁-C₄-alkylcarbonylamino-, C₁-C₄-alkoxycarbonylamino-,        C₁-C₄-alkoxy-C₁-C₄-alkyl-, C₁-C₄-haloalkoxy-C₁-C₄-alkyl-,        C₂-C₄-alkenyl-, C₂-C₄-alkynyl-, C₃-C₆-cycloalkyl-C₁-C₄-alkyl-,        C₁-C₄-alkylcarbonyl-, C₁-C₄-alkoxycarbonyl- or        aminocarbonyl-substituted aryl, heteroaryl, aryl-C₁-C₄-alkyl and        heteroaryl-C₁-C₄-alkyl, or NR′R″ in which R′ and R″ are each        independently a radical from the group of hydrogen and        C₁-C₄-alkyl, and R³ is especially a radical from the group of        methyl, ethyl, i-propyl, CF₃, CHF₂, CH₂F, CH₂CF₃, cyclopropyl,        dimethylamino, diethylamino, phenyl and benzyl.

-   R⁷ is a radical from the group of in each case optionally halogen-,    C₁-C₄-alkoxy-, C₁-C₄-haloalkoxy-, C₁-C₄-alkylthio-,    C₁-C₄-haloalkylthio-, C₁-C₄-alkylsulphinyl-,    C₁-C₄-haloalkylsulphinyl-, C₁-C₄-alkylsulphonyl- and    C₁-C₄-haloalkylsulphonyl-substituted C₁-C₄-alkyl, C₁-C₄-alkenyl and    C₂-C₄-alkynyl, in each case optionally halogen; C₁-C₄-alkyl,    C₁-C₄-haloalkyl-, C₁-C₄-alkoxy-, C₁-C₄-haloalkoxy-substituted    C₁-C₄-cycloalkyl, C₃-C₆-cycloalkyl-C₁-C₄-alkyl and    C₃-C₄-cycloalkenyl, in which the rings may contain at least one    heteroatom from the group of sulphur, oxygen (where oxygen atoms    must not be immediately adjacent) and nitrogen (and is especially

-   -   where the arrow in each case marks the bond to the sulphur atom        in the (E) radical), in each case optionally halogen-, cyano-        (including in the alkyl moiety), nitro-, C₁-C₄-alkyl-,        C₁-C₄-haloalkyl-, C₃-C₆-cycloalkyl-, C₁-C₄-alkoxy-,        C₁-C₄-haloalkoxy-, C₁-C₄-alkylthio-, C₁-C₄-haloalkylthio-,        C₁-C₄-alkylsulphinyl-, C₁-C₄-haloalkylsulphinyl-,        C₁-C₄-alkylsulphonyl-, C₁-C₄-haloalkylsulphonyl-, amino-,        C₁-C₄-alkylamino-, di(C₁-C₄-alkyl)amino-,        C₁-C₄-alkylcarbonylamino-, C₁-C₄-alkoxycarbonylamino-,        C₁-C₄-alkoxy-C₁-C₄-alkyl-, C₁-C₄-haloalkoxy-C₁-C₄-alkyl-,        C₂-C₄-alkenyl-, C₂-C₄-alkynyl-, C₃-C₆-cycloalkyl-C₁-C₄-alkyl-,        C₁-C₄-alkylcarbonyl-, C₁-C₄-alkoxycarbonyl- or        aminocarbonyl-substituted aryl, heteroaryl, aryl-C₁-C₄-alkyl and        heteroaryl-C₁-C₄-alkyl, or NR′R″ in which R′ and R″ are each        independently a radical from the group of hydrogen and        C₁-C₄-alkyl, and R⁷ is especially a radical from the group of        methyl, ethyl, i-propyl, CF₃, CHF₂, CH₂F, CH₂CF₃, cyclopropyl,        dimethylamino, diethylamino, phenyl and benzyl.

-   R¹³ is a radical from the group of hydrogen, C₁-C₄-alkyl,    C₁-C₄-haloalkyl, cyano, C₁-C₄-cyanoalkyl, C₁-C₄-hydroxyalkyl,    hydroxyl, C₁-C₄-alkoxy, C₁-C₄-alkoxy-C₁-C₄-alkyl,    C₁-C₄-alkylthio-C₁-C₄-alkyl, C₁-C₄-alkenyl, C₂-C₄-haloalkenyl,    C₂-C₄-cyanoalkenyl, C₂-C₄-alkynyl, C₂-C₄-haloalkynyl,    C₂-C₄-cyanoalkynyl, C₁-C₅-alkylcarbonyl and C₁-C₅-alkoxycarbonyl.

-   Y³ is a radical from the group of C₁-C₄-alkoxy, C₁-C₄-haloalkoxy,    C₁-C₄-alkylthio, C₁-C₄-haloalkylthio and NR¹⁴R¹⁵ where R¹⁴ and R¹⁴    an R¹⁵ are each independently a radical from the group of hydrogen,    C₁-C₄-alkyl, C₃-C₆-cycloalkyl, C₃-C₆-cycloalkyl-C₁-C₄-alkyl,    C₁-C₄-haloalkyl, cyano, C₁-C₄-cyanoalkyl, hydroxyl, C₁-C₄-alkoxy,    C₁-C₄-haloalkoxy, C₁-C₄-hydroxyalkyl, C₁-C₄-alkoxy-C₁-C₄-alkyl,    C₁-C₄-alkylthio-C₁-C₄-alkyl, C₂-C₄-alkenyl, C₂-C₄-haloalkenyl,    C₂-C₄-cyanoalkenyl, C₂-C₄-alkynyl, C₂-C₄-haloalkynyl,    C₂-C₄-cyanoalkynyl, C₁-C₅-alkylcarbonyl and C₁-C₅-alkoxycarbonyl, or    R¹⁴ and R¹⁵ together with the nitrogen atom to which they are bonded    may form an optionally halogen-, cyano-, C₁-C₄-alkyl-,    C₁-C₄-haloalkyl-, C₁-C₄-alkoxy-, C₃-C₆-cycloalkyl- or    C₁-C₄-thioalkyl-substituted saturated or unsaturated five- to    six-membered ring which may contain a further atom from the group of    sulphur, oxygen and nitrogen and/or a carbonyl group; R¹⁴ and R¹⁵    together with the nitrogen atom to which they are bonded may    especially be a radical from the group of

-   -   (in which the arrow in each case marks the bond to the carbon        atom in the (N) radical).

In the preferred definitions, unless stated otherwise,

halogen is selected from the group of fluorine, chlorine, bromine andiodine, preferably in turn from the group of fluorine, chlorine andbromine,aryl (including as part of a larger unit, for example arylalkyl) isselected from the group of phenyl, naphthyl, anthryl, phenanthrenyl, andis preferably in turn phenyl,hetaryl (synonymous with heteroaryl, including as part of a larger unit,for example hetarylalkyl) is selected from the group of furyl, thienyl,pyrrolyl, pyrazolyl, imidazolyl, 1,2,3-triazolyl, 1,2,4-triazolyl,oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, 1,2,3-oxadiazolyl,1,2,4-oxadiazolyl, 1,3,4-oxadiazolyl, 1,2,5-oxadiazolyl,1,2,3-thiadiazolyl, 1,2,4-thiadiazolyl, 1,3,4-thiadiazolyl,1,2,5-thiadiazolyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl,1,2,3-triazinyl, 1,2,4-triazinyl, 1,3,5-triazinyl, benzofuryl,benzisofuryl, benzothienyl, benzisothienyl, indolyl, isoindolyl,indazoyl, benzothiazolyl, benzisothiazolyl, benzoxazolyl,benzisoxazolyl, benzimidazolyl, 2,1,3-benzoxadiazole, quinolinyl,isoquinolinyl, cinnolinyl, phthalazinyl, quinazolinyl, quinoxalinyl,naphthyridinyl, benzotriazinyl, purinyl, pteridinyl and indolizinyl,5-membered heterocyclyl is a partially saturated 5-membered ring whichcontains 1 or 2 nitrogen atoms and/or one oxygen atom and/or one sulphuratom,6-membered heterocyclyl is a partially saturated 6-membered ring whichcontains 1 or 2 nitrogen atoms and/or one oxygen atom and/or one sulphuratom.

In the particularly preferred definitions, unless stated otherwise,

halogen is selected from the group of fluorine, chlorine, bromine andiodine, preferably in turn from the group of fluorine, chlorine andbromine,aryl (including as part of a larger unit, for example arylalkyl) isselected from the group of phenyl, naphthyl, anthryl, phenanthrenyl, andis preferably in turn phenyl,hetaryl (including as part of a larger unit, for example hetarylalkyl)is selected from the group of pyridyl, pyrimidyl, oxadiazolyl, oxazolyl,pyrazinyl, imidazolyl, thiazolyl, thiadiazolyl and furanyl.

In the very particularly preferred definitions, unless stated otherwise,

aryl is phenyl andhetaryl (equivalent to heteroaryl, including as part of a larger unit,for example hetarylalkyl) is a radical selected from the group ofpyrazolyl, oxazolyl, thiazolyl, pyridyl, pyrimidinyl, pyridazinyl andpyrazinyl.

Halogen-substituted radicals, for example haloalkyl, mono- orpolyhalogenate, up to the maximum number of possible substituents. Inthe case of polyhalogenation, the halogen atoms may be identical ordifferent. In this case, halogen is fluorine, chlorine, bromine oriodine, especially fluorine, chlorine or bromine.

Saturated or unsaturated hydrocarbyl radicals, such as alkyl or alkenyl,may in each case be straight-chain or branched as far as possible,including in combination with heteroatoms, as, for example, in alkoxy.

Optionally substituted radicals may be mono- or polysubstituted, wherethe substituents in the case of polysubstitution may be the same ordifferent.

In the radicals (A), (B), (C) and (D) that G² can represent, the arrowin each case marks the bond to the adjacent ring.

In an emphasized group of inventive compounds, G² is the radical (A).

In a further emphasized group of inventive compounds, G² is the radical(B).

In a further emphasized group of inventive compounds, G² is the radical(C).

In a further emphasized group of inventive compounds, G² is the radical(D).

In a further emphasized group of inventive compounds, X is oxygen.

In a further emphasized group of inventive compounds, X is sulphur.

In a further emphasized group of inventive compounds, G¹ is C—H.

In a further emphasized group of inventive compounds, G¹ is C—F.

In a further emphasized group of inventive compounds, G¹ is N(nitrogen).

In a further emphasized group of inventive compounds, A¹ is hydrogen.

In a further emphasized group of inventive compounds, A² is hydrogen.

In a further emphasized group of inventive compounds, n is 2.

In a further emphasized group of inventive compounds, R¹ is hydrogen.

In a further emphasized group of inventive compounds, R¹ is methyl.

In a further emphasized group of inventive compounds, R¹ is fluorine.

In a further emphasized group of inventive compounds, G⁴ is the radical(E).

In a further emphasized group of inventive compounds, G⁴ is the radical(I).

In a further emphasized group of inventive compounds, G⁴ is the radical(L).

In a further emphasized group of inventive compounds, G⁴ is the radical(N).

In a further emphasized group of inventive compounds, G³ is a pyrazolylradical.

In a further emphasized group of inventive compounds, G³ is a thiazolylradical.

In a further emphasized group of inventive compounds, G³ is a triazolylradical.

In a further emphasized group of inventive compounds, G³ is a pyridinylradical.

In a further emphasized group of inventive compounds, G³ is apyrimidinyl radical.

An emphasized embodiment of the invention relates to compounds of theformula (IA)

in which

G¹ is C—H, C—F, C—Cl or N,

R¹ is hydrogen or methyl andG⁴ is one of the (E), (L) and (N) radicals and especially the (E)radical.A group of compounds preferred among the compounds of the formula (IA)are those in which G¹ is C—F, R¹ is hydrogen and G⁴ is the (E) radical.

A further emphasized embodiment of the invention relates to compounds ofthe formula (IB)

in which

G¹ is C—H, C—F, C—Cl or N and

G⁴ is one of the (E), (L) and (N) radicals.

A further emphasized embodiment of the invention relates to compounds ofthe formula (IC)

in which

G¹ is C—H, C—F, C—Cl or N,

R¹ is hydrogen or methyl,B is hydrogen andG⁴ is one of the (E), (L) and (N) radicals.

A further emphasized embodiment of the invention relates to compounds ofthe formula (ID)

in which

G¹ is C—H, C—F, C—Cl or N,

R¹ is hydrogen or methyl,B is hydrogen andG⁴ is one of the (E) and (L) radicals.

The substituents in the (E), (L) and (N) radicals in the compounds ofthe formulae (IA), (IB), (IC) and (ID) may each assume the definitionsspecified in the description above.

The radical definitions or illustrations given above in general terms orwithin areas of preference apply to the end products of the formula (I)(and hence to the compounds of the formulae (Ia), (Ib), (IA), (IB), (IC)and (ID)) and correspondingly to starting materials and intermediates.These radical definitions can be combined with one another as desired,i.e. including combinations between the respective preferred ranges.

Preference is given in accordance with the invention to compounds of theformula (I) in which a combination of the definitions listed above aspreferred is present.

Particular preference is given in accordance with the invention tocompounds of the formula (I) in which a combination of the definitionslisted above as particularly preferred is present.

Very particular preference is given in accordance with the invention tocompounds of the formula (I) in which a combination of the definitionslisted above as very particularly preferred is present.

The preparation of the inventive compounds is explained in detailhereinafter.

The compounds of the formula (II₁), (II₂), (II₃), (II₄) and (II₅) inwhich G² represents the radicals (A), (B) and (C), which are required asstarting materials, can be prepared analogously to the methods describedin WO 2010/006713 A2.

The starting compounds of the formula (II₁), (II₂), (II₃), (II₄) and(II₅) in which G² represents the radical (D), which are required asstarting materials, can be prepared analogously to the methods describedin the literature, as follows.

For example, reaction of a bromide of the formula (IV) with a pyrazoleof the formula (V) in the presence of a capper catalyst and of a basesuch as potassium carbonate gives the compounds of the formula (VI).See, for example, for 3-(4-bromopyrazol-1-yl)pyridine: Journal ofHeterocyclic Chemistry 1981, 18, 9-14; European Journal of OrganicChemistry, 2004, 695. These pyrazoles of the formula (VI) are used toobtain, by reaction with bromine or N-bromosuccinimide, the bromides ofthe formula (VII). See, for example, for3-(4-bromopyrazol-1-yl)pyridine: Journal of Heterocyclic Chemistry 18,1981, 9-14. The bromides of the formula (VII) are used to obtain, byreaction with, for example, bis(pinacolato)diborane in the presence of apalladium catalyst and of base, the boronic esters of the formula(VIII). The starting compounds of the formula (II) required can beobtained from the bromides of the formula (VII) by reaction with acompound of the formula (X), which constitutes an H-G³-R unit whichcontains an N—H, for example a pyrazole, in the presence of a coppercatalyst and of a base, or according to the same process by reaction ofthe bromides of the formula (IV) with a suitable pyrazole of the formula(IX).

In addition, inventive compounds of the formula (I) can be obtained byreaction of the boronic esters of the formula (VIII) with a halide ofthe formula (XI) in the presence of a palladium catalyst and of a base(Suzuki reaction).

When R is a protected carboxylic acid, for example an ester, thecarboxylic acid (II₁) can be prepared easily by known methods.

When R is a protected amine, the amine (II₂) can be prepared easily byknown methods.

When R is halogen, for example bromine, (analogously to WO2007/45588 A1and US2008/318941), the halogen can be exchanged for a metal, forexample lithium. The metal compound reacts with sulphur dioxide and thenwith a chlorinating reagent such as sulphuryl chloride orN-chlorosuccinimide to give the starting compound (II₃).

where R¹³ is

The amine derivatives of the formula (III_(E-G), III_(M)) required asstarting materials are known or can be prepared by methods known inprinciple.

The acids of the formula (II₁) can be reacted, after activation, forexample to give the acid chloride (see, for example, Bioorg & MedChemLetters 15, 4354 (2005)), or by means of activating reagents such as CDI(carbonyldiimidazole; see, for example, Bioorg & MedChem 9, 1543 (2001),EDC (1-ethyl-3-[3-dimethylaminopropyl]carbodiimide hydrochloride) in thepresence of DMAP (dimethylaminopyridine; see, for example, J. Med. Chem.50, 3101 (2007)), or DCC (dicyclohexylcarbodiimide) in the presence ofHOBT (1-hydroxybenzotriazole; see, for example, J. Med. Chem. 50, 3101(2007)), with sulphonamides of the formula (III_(E)), optionally in thepresence of a base such as a metal hydride (especially sodium hydride)or DBU (diazabicycloundecene), to give the inventive compounds of theformula (I_(E)) in which X is oxygen.

The further radicals mentioned for R¹³ can be prepared from the acids ofthe formula (II_(I)) or the acid chlorides thereof by means ofliterature methods, or analogously to these methods, for example reactedwith compounds of the formula (III_(F)) according to Chem. Letters 36,1370 (2007) or J. Med. Chem. 29, 1299 (1986) to give the inventivecompounds of the formula (I_(F)), or, for example, with compounds of theformula (III_(G)) according to J. Org. Chem. 72, 465 (2007) orPhosphorus & Sulfur 20, 93 (1984) to give the inventive compounds of theformula (I_(G)) and, for example, with cyanamines of the formula(III_(M)) according to WO2006/002099 A2 to give the inventive compoundsof the formula (I_(M)).

Compounds of the formula (I_(H)) can be prepared, for example, byreacting the carboxamides of the formula (II_(H)) with sulphoxides ofthe formula (III_(H)) by means of literature methods or analogousmethods; see, for example, WO 2008/154528 A2.

The carboxamides of the formula (II_(H)) required as starting materialscan be prepared from the acids (II₁) or the acid chlorides by means ofliterature methods or analogous methods, for example as described in WO2007/103755 A2 or US 2009/203657 A1.

The sulphoxides of the formula (III_(H)) are compounds known from theliterature.

Compounds of the formula (I₁) can be prepared, for example, by reactingthe amines of the formula (II₂) with compounds of the formula (III_(I1))or (III_(I2)), analogously to the methods described in WO2007/132475 A1or WO2006/019831 A1.

The compounds of the formula (III_(I1)) and (III_(I2)) are known or canbe prepared by methods known in principle.

Compounds of the formula (I_(J)) can be prepared, for example, byreacting, heterocyclic amines of the formula (II₂) with sulphonylchlorides of the formula (III_(J)) in the presence of a base, forexample pyridine or sodium hydroxide; cf., for example, WO 2007/114532A1 and US 2006/211603 A1.

The chlorosulphinyl or chlorosulphonyl derivatives of the formula(III_(J)) required as starting materials are known or can be prepared bymethods known in principle.

Compounds of the formula (I_(K)) can be prepared, for example, byreacting the sulphonyl chlorides of the formula (II₃) with amines of theformula (III_(K)), optionally in the presence of a base, for examplepyridine or triethylamine, analogously to the methods described in U.S.Pat. No. 6,265,411, WO 2007/114532 A1 or U.S. Pat. No. 6,673,817.

The amines of the formula (III_(K)) required as starting materials areknown or can be prepared by methods known in principle.

Compounds of the formula (I_(L)) in which X is oxygen can be prepared,for example, by reacting sulphonyl chlorides of the formula (II₃) withamides of the formula (III_(L)) in the presence of a base, for examplesodium hydride or n-butyllithium, analogously to the methods describedin US2004/006143 or Org. Let. 3458-3461 (2009).

The amides of the formula (III_(L)) required as starting materials areknown or can be prepared by methods known in principle.

Compounds of the formula (I_(N)) can be prepared, for example, byreaction of nitriles of the formula (II₄) or thio amides of the formula(II₅) with oxy, thio or amino derivatives of the formula (III_(N)). Oxyderivatives can be used, for example, by the methods described inEuropean Journal of Medicinal Chemistry 2009, 44(6), 2497-2505; thioderivatives can be used, for example, by the methods described inJournal of the America Chemical Society 1985, 107(28), 5745-5754. Aminoderivatives can be used, for example, by the methods described inBioorganic & Medicinal Chemistry Letter 2010, 20(1), 299-301,WO2007/083239 A1 or European Journal of Medicinal Chemistry 2010, 45(3),902-908.

The compounds of the formula (III_(N)) required as starting materialsare known or can be prepared by methods known in principle.

Compounds of the formula (I_(E-H)), (I_(I)) and (I_(L)) in which X issulphur can be prepared from the corresponding compounds of the formula(I_(E-H)), (I_(I)) and (I_(L)) in which X is oxygen by reaction with athionating reagent. The sulphiding agents (thionating reagents) used arepreferably phosphorus reagents, for example diphosphorus pentasulphide(P₂S₅), diphosphorus pentasulphide/pyridine (P₂S₅/Py), diphosphoruspentasulphide/triethylamine (P₂S₅/NEt₃), diphosphoruspentasulphide/sodium hydrogencarbonate (P₂S₅/NaHCO₃ “Scheeren'sreagent”), or more preferably2,4-bis(4-methoxyphenyl)-2,4-dithioxo-1,3,2,4-dithiadiphosphetane“Lawesson's Reagent (LR)”,2,4-bis(4-phenoxyphenyl)-2,4-dithioxo-1,3,2,4-dithiadiphosphetane“Belleau's reagent (BR)” or2,4-bis(4-phenylthiophenyl)-2,4-dithioxo-1,3,2,4-dithiadiphosphetane.

N-Oxides can be obtained, for example, by reacting compounds of theformula (I) with mCPBA (meta-chloroperbenzoic acid). Salts of compoundsof the formula (I) are obtainable by reacting compounds of the formula(I) with compounds of the formula RX in which X is, for example, halogensuch as chlorine or bromine and R is, for example, an in each caseoptionally substituted alkyl, alkenyl or alkynyl radical.

The intermediates of the formulae (XII), (XIII), (XIV), (XV), (XVI),(XVII) and (XVIII) which follow are novel and also form part of thesubject-matter of the invention.

Compounds of the formula (XII)

in whichR¹⁶ is fluorine, chlorine, bromine or iodine (especially chlorine,bromine or iodine) andX, R² and R are each as defined above.

Particular mention should be made of the following compounds of theformula (XII).

where R¹ is methyl, ethyl, cyclopropyl, CF₃, CH₂CF₃, dimethylamino,diethylamino, phenyl or benzyl.

Compounds of the formula (XIII)

in which G¹ is nitrogen, C-halogen, C-cyano, C-nitro, C-alkyl,C-cycloalkyl or C-alkoxy, preferably nitrogen, C-halogen, C-cyano,C-nitro, C—C₁-C₆-alkyl, C—C₃-C₆-cycloalkyl or C—C₁-C₆-alkoxy.

Particular mention should be made of the following compounds of theformula (XIII).

Compounds of the formula (XIV)

in whichR¹⁶ is fluorine, chlorine, bromine or iodine (especially chlorine,bromine or iodine) andX, R² and R⁵ are each as defined above.

Particular mention should be made of the following compounds of theformula (XIV):

where R⁵ is a radical from the group of methyl, ethyl, i-propyl, CF₃,CHF₂, CH₂F, CH₂CF₃, cyclopropyl, dimethylamino, diethylamino, phenyl andbenzyl.

Compounds of the formula (XV)

in whichR¹⁶ is fluorine, chlorine, bromine or iodine (especially chlorine,bromine or iodine) andX, R² and R⁷ are each as defined above.

Particular mention should be made of the following compounds of theformula (XV):

where R⁷ is methyl, ethyl, cyclopropyl, CF₃, CH₂CF₃, dimethylamino,diethylamino, phenyl or benzyl.

Compounds of the formula (XVI)

in whichR¹⁶ is fluorine, chlorine, bromine or iodine (especially chlorine,bromine or iodine) andX, R² and R⁷ are each as defined above.

Particular mention should be made of the following compounds of theformula (XVI):

where R⁷ is as defined above and is especially methyl, ethyl,cyclopropyl, CF₃, CH₂CF₃, dimethylamino, diethylamino, phenyl or benzyl.

Compounds of the formula (XVII)

in which

-   G¹ is nitrogen, C-halogen, C-cyano, C-nitro, C-alkyl, C-cycloalkyl    or C-alkoxy, preferably nitrogen, C-halogen, C-cyano, C-nitro,    C—C₁-C₆-alkyl, C—C₃-C₆-cycloalkyl or C—C₁-C₆-alkoxy and-   R² is as defined above.

Particular mention should be made of the following compounds of theformula (XVII).

Compounds of the formula (XVIII)

in which

-   G¹ is nitrogen, C-halogen, C-cyano, C-nitro, C-alkyl, C-cycloalkyl    or C-alkoxy, preferably nitrogen, C-halogen, C-cyano, C-nitro,    C—C₁-C₆-alkyl, C—C₃-C₆-cycloalkyl or C—C₁-C₆-alkoxy and-   R² is as defined above.

Particular mention should be made of the following compounds of theformula (XVIII):

The inventive active ingredients, given good plant tolerance, favourablehomeotherm toxicity and good environmental compatibility, are suitablefor protecting plants and plant organs, for increasing harvest yields,for improving the quality of the harvested material and for controllinganimal pests, especially insects, arachnids, helminths, nematodes andmolluscs, which are encountered in agriculture, in horticulture, inanimal husbandry, in forests, in gardens and leisure facilities, in theprotection of stored products and of materials, and in the hygienesector. They can preferably be used as crop protection compositions.They are active against normally sensitive and resistant species andagainst all or some stages of development. The abovementioned pestsinclude:

From the order of the Anoplura (Phthiraptera), for example, Damaliniaspp., Haematopinus spp., Linognathus spp., Pediculus spp., Trichodectesspp.

From the class of the Arachnida, for example, Acarus siro, Aceriasheldoni, Aculops spp., Aculus spp., Amblyomma spp., Argas spp.,Boophilus spp., Brevipalpus spp., Bryobia praetiosa, Chorioptes spp.,Dermanyssus gallinae, Eotetranychus spp., Epitrimerus pyri,Eutetranychus spp., Eriophyes spp., Hemitarsonemus spp., Hyalomma spp.,Ixodes spp., Latrodectus mactans, Metatetranychus spp., Oligonychusspp., Ornithodoros spp., Panonychus spp., Phyllocoptruta oleivora,Polyphagotarsonemus latus, Psoroptes spp., Rhipicephalus spp.,Rhizoglyphus spp., Sarcoptes spp., Scorpio maurus, Stenotarsonemus spp.,Tarsonemus spp., Tetranychus spp., Vasates lycopersici.

From the class of the Bivalva, for example, Dreissena spp.

From the order of the Chilopoda, for example, Geophilus spp., Scutigeraspp.

From the order of the Coleoptera, for example, Acanthoscelides obtectus,Adoretus spp., Agelastica alni, Agriotes spp., Amphimallon solstitialis,Anobium punctatum, Anoplophora spp., Anthonomus spp., Anthrenus spp.,Apogonia spp., Atomaria spp., Attagenus spp., Bruchidius obtectus,Bruchus spp., Ceuthorhynchus spp., Cleonus mendicus, Conoderus spp.,Cosmopolites spp., Costelytra zealandica, Curculio spp., Cryptorhynchuslapathi, Dermestes spp., Diabrotica spp., Epilachna spp., Faustinuscubae, Gibbium psylloides, Heteronychus arator, Hylamorpha elegans,Hylotrupes bajulus, Hypera postica, Hypothenemus spp., Lachnosternaconsanguinea, Leptinotarsa decemlineata, Lissorhoptrus oryzophilus,Lixus spp., Lyctus spp., Meligethes aeneus, Melolontha melolontha,Migdolus spp., Monochamus spp., Naupactus xanthographus, Niptushololeucus, Oryctes rhinoceros, Oryzaephilus surinamensis, Otiorrhynchussulcatus, Oxycetonia jucunda, Phaedon cochleariae, Phyllophaga spp.,Popillia japonica, Premnotrypes spp., Psylliodes chrysocephala, Ptinusspp., Rhizobius ventralis, Rhizopertha dominica, Sitophilus spp.,Sphenophorus spp., Sternechus spp., Symphyletes spp., Tenebrio molitor,Tribolium spp., Trogoderma spp., Tychius spp., Xylotrechus spp., Zabrusspp.

From the order of the Collembola, for example, Onychiurus armatus.

From the order of the Dermaptera, for example, Forficula auricularia.

From the order of the Diplopoda, for example, Blaniulus guttulatus.

From the order of the Diptera, for example, Aedes spp., Anopheles spp.,Bibio hortulanus, Calliphora erythrocepha, Ceratitis capitata,Chrysomyia spp., Cochliomyia spp., Cordylobia anthropophaga, Culex spp.,Cuterebra spp., Dacus oleae, Dermatobia hominis, Drosophila spp., Fanniaspp., Gastrophilus spp., Hylemyia spp., Hyppobosca spp., Hypoderma spp.,Liriomyza spp. Lucilia spp., Musca spp., Nezars spp., Oestrus spp.,Oscinella frit, Pegomyia hyoscyami, Phorbia spp., Stomoxys spp., Tabanusspp., Tannia spp., Tipula paludosa, Wohlfahrtia spp.

From the class of the Gastropoda, for example, Arion spp., Biomphalariaspp., Bulinus spp., Deroceras spp., Galba spp., Lymnaea spp.,Oncomelania spp., Succinea spp.

From the class of the helminths, for example, Ancylostoma duodenale,Ancylostoma ceylanicum, Acylostoma braziliensis, Ancylostoma spp.,Ascaris lubricoides, Ascaris spp., Brugia malayi, Brugia timori,Bunostomum spp., Chabertia spp., Clonorchis spp., Cooperia spp.,Dicrocoelium spp., Dictyocaulus filaria, Diphyllobothrium latum,Dracunculus medinensis, Echinococcus granulosus, Echinococcusmultilocularis, Enterobius vermicularis, Faciola spp., Haemonchus spp.,Heterakis spp., Hymenolepis nana, Hyostrongulus spp., Loa Loa,Nematodirus spp., Oesophagostomum spp., Opisthorchis spp., Onchocercavolvulus, Ostertagia spp., Paragonimus spp., Schistosomen spp.,Strongyloides fuelleborni, Strongyloides stercoralis, Stronyloides spp.,Taenia saginata, Taenia solium, Trichinella spiralis, Trichinellanativa, Trichinella britovi, Trichinella nelsoni, Trichinellapseudopsiralis, Trichostrongulus spp., Trichuris trichuria, Wuchereriabancrofti.

It is also possible to control protozoa, such as Eimeria.

From the order of the Heteroptera, for example, Anasa tristis,Antestiopsis spp., Blissus spp., Calocoris spp., Campylomma livida,Cavelerius spp., Cimex spp., Creontiades dilutus, Dasynus piperis,Dichelops ftrcatus, Diconocoris hewetti, Dysdercus spp., Euschistusspp., Eurygaster spp., Heliopeltis spp., Horcias nobilellus, Leptocorisaspp., Leptoglossus phyllopus, Lygus spp., Macropes excavatus, Miridae,Nezara spp., Oebalus spp., Pentomidae, Piesma quadrata, Piezodorus spp.,Psallus seriatus, Pseudacysta persea, Rhodnius spp., Sahlbergellasingularis, Scotinophora spp., Stephanitis nashi, Tibraca spp., Triatomaspp.

From the order of the Homoptera, for example, Acyrthosipon spp.,Aeneolamia spp., Agonoscena spp., Aleurodes spp., Aleurolobusbarodensis, Aleurothrixus spp., Amrasca spp., Anuraphis cardui,Aonidiella spp., Aphanostigma piri, Aphis spp., Arboridia apicalis,Aspidiella spp., Aspidiotus spp., Atanus spp., Aulacorthum solani,Bemisia spp., Brachycaudus helichrysii, Brachycolus spp., Brevicorynebrassicae, Calligypona marginata, Carneocephala fulgida, Ceratovacunalanigera, Cercopidae, Ceroplastes spp., Chatosiphon fragaefolii,Chionaspis tegalensis, Chlorita onukii, Chromaphis juglandicola,Chrysomphalus ficus, Cicadulina mbila, Coccomytilus halli, Coccus spp.,Cryptomyzus ribis, Dalbulus spp., Dialeurodes spp., Diaphorina spp.,Diaspis spp., Doralis spp., Drosicha spp., Dysaphis spp., Dysmicoccusspp., Emposca spp., Eriosoma spp., Erythroneura spp., Euscelisbilobatus, Geococcus coffeae, Homalodisca coagulata, Hyalopterusarundinis, Icerya spp., Idiocerus spp., Idioscopus spp., Laodelphaxstriatellus, Lecanium spp., Lepidosaphes spp., Lipaphis erysimi,Macrosiphum spp., Mahanarva fimbriolata, Melanaphis sacchari,Metcalfiella spp., Metopolophium dirhodum, Monellia costalis,Monelliopsis pecanis, Myzus spp., Nasonovia ribisnigri, Nephotettixspp., Nilaparvata lugens, Oncometopia spp., Orthezia praelonga,Parabemisia myricae, Paratrioza spp., Parlatoria spp., Pemphigus spp.,Peregrinus maidis, Phenacoccus spp., Phioeomyzus passerinii, Phorodonhumuli, Phylloxera spp., Pinnaspis aspidistrae, Planococcus spp.,Protopulvinaria pyriformis, Pseudaulacaspis pentagona, Pseudococcusspp., Psylla spp., Pteromalus spp., Pyrilla spp., Quadraspidiotus spp.,Quesada gigas, Rastrucoccus spp., Rhopalosiphum spp., Saissetia spp.,Scaphoides titanus, Schizaphis graminum, Selenaspidus articulatus,Sogata spp., Sogatella furcifera, Sogatodes spp., Stictocephala festina,Tenalaphara malayensis, Tinocallis caryaefoliae, Tomaspis spp.,Toxoptera spp., Trialeurodes vaporariorum, Trioza spp., Typhlocyba spp.,Unaspis spp., Viteus vitifolii.

From the order of the Hymenoptera, for example, Diprion spp., Hoplocampaspp., Lasius spp., Monomorium pharaonis and Vespa spp.

From the order of the Isopoda, for example, Armadillidium vulgare,Oniscus asellus and Porcellio scaber.

From the order of the Isoptera, for example, Reticulitermes spp. andOdontotermes spp.

From the order of the Lepidoptera, for example, Acronicta major, Aedialeucomelas, Agrotis spp., Alabama argillacea, Anticarsia spp. Barathrabrassicae, Bucculatrix thurberiella, Bupalus piniarius, Cacoecia podana,Capua reticulana, Carpocapsa pomonella, Chematobia brumata, Chilo spp.,Choristoneura fumiferana, Clysia ambiguella, Cnaphalocerus spp., Eariasinsulana, Ephestia kuehniella, Euproctis chrysorrhoea, Euxoa spp.,Feltia spp., Galleria mellonella, Helicoverpa spp., Heliothis spp.,Hofmannophila pseudospretella, Homona magnanima, Hyponomeuta padella,Laphygma spp., Lithocolletis blancardella, Lithophane antennata,Loxagrotis albicosta, Lymantria spp., Malacosoma neustria, Mamestrabrassicae, Mocis repanda, Mythimna separata, Oria spp., Oulema oryzae,Panolis flammea, Pectinophora gossypiella, Phyllocnistis citrella,Pieris spp., Plutella xylostella, Prodenia spp., Pseudaletia spp.,Pseudoplusia includens, Pyrausta nubilalis, Spodoptera spp., Thermesiagemmatalis, Tinea pellionella, Tineola bisselliella, Tortrix viridana,Trichoplusia spp.

From the order of the Orthoptera, for example, Acheta domesticus, Blattaorientalis, Blattella germanica, Gryllotalpa spp., Leucophaea maderac,Locusta spp., Melanoplus spp., Periplaneta americana, Schistocercagregaria.

From the order of the Siphonaptera, for example, Ceratophyllus spp. andXenopsylla cheopis.

From the order of the Symphyla, for example, Scutigerella immaculata.

From the order of the Thysanoptera, for example, Baliothrips biformis,Enneothrips flavens, Frankliniella spp., Heliothrips spp., Hercinothripsfemoralis, Kakothrips spp., Rhipiphorothrips cruentatus, Scirtothripsspp., Taeniothrips cardamoni and Thrips spp.

From the order of the Thysanura, for example, Lepisma saccharina.

The phytoparasitic nematodes include, for example, Anguina spp.,Aphelenchoides spp., Belonoaimus spp., Bursaphelenchus spp., Ditylenchusdipsaci, Globodera spp., Heliocotylenchus spp., Heterodera spp.,Longidorus spp., Meloidogyne spp., Pratylenchus spp., Radopholussimilis, Rotylenchus spp., Trichodorus spp., Tylenchorhynchus spp.,Tylenchulus spp., Tylenchulus semipenetrans and Xiphinema spp.

The inventive compounds can, at certain concentrations or applicationrates, also be used as herbicides, safeners, growth regulators or agentsto improve plant properties, or as microbicides, for example asfungicides, antimycotics, bactericides, viricides (including agentsagainst viroids) or as agents against MLO (mycoplasma-like organisms)and RLO (rickettsia-like organisms). They can also be used asintermediates or precursors for the synthesis of further activeingredients.

The active ingredients can be converted to the customary formulations,such as solutions, emulsions, wettable powders, water- and oil-basedsuspensions, powders, dusts, pastes, soluble powders, soluble granules,granules for broadcasting, suspoemulsion concentrates, natural compoundsimpregnated with active ingredient, synthetic substances impregnatedwith active ingredient, fertilizers and also microencapsulations inpolymeric substances.

These formulations are produced in a known manner, for example by mixingthe active ingredients with extenders, that is, liquid solvents and/orsolid carriers, optionally with the use of surfactants, that is to sayemulsifiers and/or dispersants and/or foam-formers. The formulations areprepared either in suitable facilities or else before or duringapplication.

The auxiliaries used may be those substances which are suitable forimparting particular properties to the composition itself and/or topreparations derived therefrom (for example spray liquors, seeddressings), such as certain technical properties and/or also particularbiological properties. Typical auxiliaries include: extenders, solventsand carriers.

Suitable extenders are, for example, water, polar and nonpolar organicchemical liquids, for example from the classes of the aromatic andnonaromatic hydrocarbons (such as paraffins, alkylbenzenes,alkylnaphthalenes, chlorobenzenes), the alcohols and polyols (which mayoptionally also be substituted, etherified and/or esterified), theketones (such as acetone, cyclohexanone), esters (including fats andoils) and (poly)ethers, the unsubstituted and substituted amines,amides, lactams (such as N-alkylpyrrolidones) and lactones, thesulphones and sulphoxides (such as dimethyl sulphoxide).

If the extender utilized is water, it is also possible to use, forexample, organic solvents as auxiliary solvents. Useful liquid solventsessentially include: aromatics such as xylene, toluene oralkylnaphthalenes, chlorinated aromatics and chlorinated aliphatichydrocarbons such as chlorobenzenes, chloroethylenes or methylenechloride, aliphatic hydrocarbons such as cyclohexane or paraffins, forexample petroleum fractions, mineral and vegetable oils, alcohols suchas butanol or glycol and also their ethers and esters, ketones such asacetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone,strongly polar solvents such as dimethyl sulphoxide, and also water.

Useful solid carriers include:

for example ammonium salts and natural rock flours, such as kaolins,clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceousearth, and synthetic rock flours, such as finely divided silica, aluminaand silicates; useful solid carriers for granules include: for example,crushed and fractionated natural rocks such as calcite, marble, pumice,sepiolite and dolomite, and also synthetic granules of inorganic andorganic flours, and granules of organic material such as paper, sawdust,coconut shells, maize cobs and tobacco stalks; useful emulsifiers and/orfoam-formers include: for example nonionic and anionic emulsifiers, suchas polyoxyethylene fatty acid esters, polyoxyethylene fatty alcoholethers, for example alkylaryl polyglycol ethers, alkylsulphonates, alkylsulphates, arylsulphonates and also protein hydrolysates; suitabledispersants are nonionic and/or ionic substances, for example from theclasses of the alcohol-POE and/or -POP ethers, acid and/or POP POEesters, alkylaryl and/or POP POE ethers, fat and/or POP POE adducts,POE- and/or POP-polyol derivatives, POE- and/or POP-sorbitan or -sugaradducts, alkyl or aryl sulphates, alkyl- or arylsulphonates and alkyl oraryl phosphates or the corresponding PO-ether adducts. Additionallysuitable are oligo- or polymers, for example those derived from vinylicmonomers, from acrylic acid, from EO and/or PO alone or in combinationwith, for example, (poly)alcohols or (poly)amines. It is also possibleto use lignin and its sulphonic acid derivatives, unmodified andmodified celluloses, aromatic and/or aliphatic sulphonic acids and alsotheir adducts with formaldehyde.

In the formulations it is possible to use tackifiers such ascarboxymethylcellulose, natural and synthetic polymers in the form ofpowders, granules or lattices, such as gum arabic, polyvinyl alcohol andpolyvinyl acetate, or else natural phospholipids such as cephalins andlecithins and synthetic phospholipids.

It is possible to use dyes such as inorganic pigments, for example ironoxide, titanium oxide and Prussian Blue, and organic dyes such asalizarin dyes, azo dyes and metal phthalocyanine dyes, and tracenutrients such as salts of iron, manganese, boron, copper, cobalt,molybdenum and zinc.

Further additives may be perfumes, mineral or vegetable, optionallymodified oils, waxes and nutrients (including trace nutrients), such assalts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.

Additional components may be stabilizers, such as cold stabilizers,preservatives, antioxidants, light stabilizers, or other agents whichimprove chemical and/or physical stability.

The formulations contain generally between 0.01 and 98 percent by weightof active ingredient, preferably between 0.5 and 90%.

The inventive active ingredients may also be present, as such or intheir formulations, in a mixture with one or more suitable fungicides,bactericides, acaricides, nematicides, insecticides, microbicides,fertilizers, attractants, sterilants, synergists, safeners,semiochemicals and/or plant growth regulators, in order thus to broadenthe spectrum of activity, to prolong the duration of action, to increasethe speed of action, to prevent repellency or to preclude thedevelopment of resistance. In addition, such combinations can improveplant growth, increase tolerance to high or low temperatures, to droughtor to water content or soil salinity, enhance flowering performance,facilitate harvesting and increase yields, accelerate ripening, increasequality and/or the nutritional value of the harvested products, prolongstorage life and/or improve the processability of the harvestedproducts. In general, combination of the inventive active ingredientsand mixing partners gives synergistic effects, which means that theefficacy of the particular mixture is greater than the efficacy of theindividual components. It is generally possible to use the combinationseither as seed applications or in premixes, tankmixes or readymixes.

Particularly favourable mixing partners are, for example, the following:

Insecticides/Acaricides/Nematicides:

The active ingredients identified here by their common name are knownand are described, for example, in the pesticide handbook (“ThePesticide Manual” 14th Ed., British Crop Protection Council 2006) or canbe found on the Internet (e.g. http://www.alanwood.net/pesticides).

(1) Acetylcholinesterase (AChE) inhibitors, for example

carbamates, for example alanycarb, aldicarb, bendiocarb, benfuracarb,butocarboxim, butoxycarboxim, carbaryl, carbofuran, carbosulfan,ethiofencarb, fenobucarb, formetanate, furathiocarb, isoprocarb,methiocarb, methomyl, metolcarb, oxamyl, pirimicarb, propoxur,thiodicarb, thiofanox, triazamate, trimethacarb, XMC and xylylcarb; ororganophosphates, for example acephate, azamethiphos, azinphos-ethyl,azinphos-methyl, cadusafos, chlorethoxyfos, chlorfenvinphos,chlormephos, chlorpyrifos, chlorpyrifos-methyl, coumaphos, cyanophos,demeton-S-methyl, diazinon, dichlorvos/DDVP, dicrotophos, dimethoate,dimethylvinphos, disulfoton, EPN, ethion, ethoprophos, famphur,fenamiphos, fenitrothion, fenthion, fosthiazate, heptenophos, imicyafos,isofenphos, isopropyl O-(methoxyaminothiophosphoryl)salicylate,isoxathion, malathion, mecarbam, methamidophos, methidathion, mevinphos,monocrotophos, naled, omethoate, oxydemeton-methyl, parathion,parathion-methyl, phenthoate, phorate, phosalone, phosmet, phosphamidon,phoxim, pirimiphos-methyl, profenofos, propetamphos, prothiofos,pyraclofos, pyridaphenthion, quinalphos, sulfotep, tebupirimfos,temephos, terbufos, tetrachlorvinphos, thiometon, triazophos, triclorfonand vamidothion.

(2) GABA-gated chloride channel antagonists, for example

cyclodieno-organochlorines, for example chlordane and endosulfan; orphenylpyrazoles (fiproles), for example ethiprole and fipronil.

(3) Sodium channel modulators/voltage-dependent sodium channel blockers,for example

pyrethroids, for example acrinathrin, allethrin, d-cis-trans allethrin,d-trans allethrin, bifenthrin, bioallethrin, bioallethrinS-cyclopentenyl isomer, bioresmethrin, cycloprothrin, cyfluthrin,beta-cyfluthrin, cyhalothrin, lambda-cyhalothrin, gamma-cyhalothrin,cypermethrin, alpha-cypermethrin, beta-cypermethrin, theta-cypermethrin,zeta-cypermethrin, cyphenothrin [(R)-trans-isomers], deltamethrin,empenthrin [(EZ)-(1R)-isomers], esfenvalerate, etofenprox,fenpropathrin, fenvalerate, flucythrinate, flumethrin, tau-fluvalinate,halfenprox, imiprothrin, kadethrin, permethrin, phenothrin[(1R)-trans-isomer], prallethrin, pyrethrins (pyrethrum), resmethrin,silafluofen, tefluthrin, tetramethrin, tetramethrin [(1R)-isomers],tralomethrin and transfluthrin; orDDT; or methoxychlor.

(4) Nicotinergic acetylcholine receptor (nAChR) agonists, for example

neonicotinoids, for example acetamiprid, clothianidin, dinotefuran,imidacloprid, niteupyram, thiacloprid and thiamethoxam; ornicotine.

(5) Nicotinergic acetylcholine receptor (nAChR) allosteric activators,for example

spinosins, for example spinetoram and spinosad.

(6) Chloride channel activators, for example

avermectins/milbemycins, for example abamectin, emamectin benzoate,lepimectin and milbemectin.

(7) Juvenile hormone imitators, for example

Juvenile hormone analogues, for example hydroprene, kinoprene andmethoprene; or fenoxycarb or pyriproxyfen.

(8) Active ingredients with unknown or nonspecific mechanisms of action,for example

alkyl halides, for example methyl bromide and other alkyl halides; orchloropicrin; or sulphuryl fluoride; or borax; or tartar emetic.

(9) Selective antifeedants, for example pymetrozine; or flonicamid.

(10) Mite growth inhibitors, for example clofentezine, hexythiazox anddiflovidazin; or etoxazole.

(11) Microbial disruptors of the insect gut membrane, for exampleBacillus thuringiensis subspecies israelensis, Bacillus sphaericus,Bacillus thuringiensis subspecies alzawai, Bacillus thuringiensissubspecies kurstaki, Bacillus thuringiensis subspecies tenebrionis andBT plant proteins: Cry1Ab, Cry1Ac, Cry1Fa, Cry2Ab, mCry3A, Cry3Ab,Cry3Bb, Cry34/35Ab1.

(12) Oxidative phosphorylation inhibitors, ATP disruptors, for examplediafenthiuron; or

organotin compounds, for example azocyclotin, cyhexatin and fenbutatinoxide; orpropargite; or tetradifon.

(13) Oxidative phosphorylation decouplers acting by interrupting the Hproton gradient, for example chlorfenapyr, DNOC and sulfluramid.

(14) Nicotinergic acetylcholine receptor antagonists, for examplebensultap, cartap-hydrochloride, thiocyclam and thiosultap-sodium.

(15) Chitin biosynthesis inhibitors, type 0, for example bistrifluoron,chlorfluazuron, diflubenzuron, flucycloxuron, flufenoxuron,hexaflumuron, lufenuron, novaluron, noviflumuron, teflubenzuron andtriflumuron.

(16) Chitin biosynthesis inhibitors, type 1, for example buprofezin;

(17) Moulting disruptors, dipteran, for example cyromazine;

(18) Ecdysone receptor agonists, for example chromafenozide,halofenozide, methoxyfenozide and tebufenozide.

(19) Octopaminergic agonists, for example amitraz;

(20) Complex-III electron transport inhibitors, for examplehydramethylnone; or acequinocyl; or fluacrypyrim;

(21) Complex-I electron transport inhibitors, for example METIacaricides, for example fenazaquin, fenpyroximate, pyrimidifen,pyridaben, tebufenpyrad and tolfenpyrad; or

rotenone (Derris).

(22) Voltage-dependent sodium channel blockers, for example indoxacarb;or metaflumizone.

(23) Inhibitors of acetyl-CoA carboxylase, for example tetronic andtetramic acid derivatives, for example spirodiclofen, spiromesifen andspirotetramat.

(24) Complex-IV electron transport inhibitors, for example phosphines,for example aluminium phosphide, calcium phosphide, phosphine and zincphosphide; or cyanide.

(25) Complex-II electron transport inhibitors, for example cyenopyrafen.

(28) Ryanodine receptor effectors, for example diamides, for examplechlorantraniliprole and flubendiamide.

Further active ingredients with unknown mechanism of action, for exampleamidoflumet, azadirachtin, benclothiaz, benzoximate, bifenazate,bromopropylate, chinomethionat, cryolite, cyantraniliprole (Cyazypyr),cyflumetofen, dicofol, diflovidazine, fluensulfone, flufenerim,flufiprole, fluopyram, flufenozide, imidaclothiz, iprodione, pyridalyl,pyrifluquinazon and iodomethane; and also products based on Bacillusfirmus (1-1582, BioNeem, Votivo) and the following known activeingredients:

3-bromo-N-{2-bromo-4-chloro-6-[(1-cyclopropylethyl)carbamoyl]phenyl}-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-carboxamide(known from WO2005/077934),4-{[(6-bromopyrid-3-yl)methyl](2-fluoroethyl)amino}furan-2(5H)-one(known from WO 2007/115644),4-{[(6-fluoropyrid-3-yl)methyl](2,2-difluoroethyl)amino}furan-2(5H)-one(known from WO 2007/115644),4-{[(2-chloro-1,3-thiazol-5-yl)methyl](2-fluoroethyl)amino}furan-2(5H)-one(known from WO 2007/115644),4-{[(6-chloropyrid-3-yl)methyl](2-fluoroethyl)amino}furan-2(5H)-one(known from WO 2007/115644),4-{[(6-chloropyrid-3-yl)methyl](2,2-difluoroethyl)amino}furan-2(5H)-one(known from WO 2007/115644),4-{[(6-chloro-5-fluoropyrid-3-yl)methyl](methyl)amino}furan-2(5H)-one(known from WO 2007/115643),4-{[(5,6-dichloropyrid-3-yl)methyl](2-fluoroethyl)amino}furan-2(5H)-one(known from WO 2007/115646),4-{[(6-chloro-5-fluoropyrid-3-yl)methyl](cyclopropyl)amino}furan-2(5H)-one(known from WO 2007/115643),4-{[(6-chloropyrid-3-yl)methyl](cyclopropyl)amino}furan-2(5H)-one (knownfrom EP-A-0 539 588),4-{[(6-chloropyrid-3-yl)methyl](methyl)amino}furan-2(5H)-one (known fromEP-A-0 539 588),{[1-(6-chloropyridin-3-yl)ethyl](methyl)oxido-λ⁴-sulphanylidene}cyanamide(known from WO 2007/149134), and its diastereomers{[(1R)-1-(6-chloropyridin-3-yl)ethyl](methyl)oxido-λ⁴-sulphanylidene}cyanamide(A) and{[(1S)-1-(6-chloropyridin-3-yl)ethyl](methyl)oxido-λ⁴-sulphanylidene}cyanamide(B) (likewise known from WO2007/149134) and sulfoxaflor (likewise knownfrom WO 2007/149134), and its diastereomers[(R)-methyl(oxido){(1R)-1-[6-(trifluoromethyl)pyridin-3-yl]ethyl}-λ⁴-sulphanylidene]cyanamide(A1) and[(S)-methyl(oxido){(1S)-1-[6-(trifluoromethyl)pyridin-3-yl]ethyl}-λ⁴-sulphanylidene]cyanamide(A2), designated as diastereomer group A (known from WO 2010/074747, WO2010/074751),[(R)-methyl(oxido){(1S)-1-[6-(trifluoromethyl)pyridin-3-yl]ethyl}-λ⁴-sulphanylidene]cyanamide(B1) and[(S)-methyl(oxido){(1R)-1-[6-(trifluoromethyl)pyridin-3-yl]ethyl}-λ⁴-sulphanylidene]cyanamide(B2), designated as diastereomer group B (likewise known from WO2010/074747, WO 2010/074751) and11-(4-chloro-2,6-dimethylphenyl)-12-hydroxy-1,4-dioxa-9-azadispiro[4.2.4.2]tetradec-11-en-10-one(known from WO 2006/089633),3-(4′-fluoro-2,4-dimethylbiphenyl-3-yl)-4-hydroxy-8-oxa-1-azaspiro[4.5]dec-3-en-2-one(known from WO 2008/067911),1-{2-fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulphinyl]phenyl}-3-(trifluoromethyl)-1H-1,2,4-triazole-5-amine(known from WO 2006/043635),[(3S,4aR,12R,12aS,12bS)-3-cyclopropylcarbonyl)oxy]-6,12-dihydroxy-4,12b-dimethyl-11-oxo-9-(pyridin-3-yl)-1,3,4,4a,5,6,6a,12,12a,12b-decahydro-2H,11H-benzo[f]pyrano[4,3-b]chromen-4-yl]methylcyclopropanecarboxylate (known from WO 2008/066153),2-cyano-3-(difluoromethoxy)-N,N-dimethylbenzenesulphonamide (known fromWO2006/056433), 2-cyano-3-(difluoromethoxy)-N-methylbenzenesulphonamide(known from WO2006/100288),2-cyano-3-(difluoromethoxy)-N-ethylbenzenesulphonamide (known fromWO2005/035486),4-(difluoromethoxy)-N-ethyl-N-methyl-1,2-benzothiazole-3-amine1,1-dioxide (known from WO2007/057407),N-[1-(2,3-dimethylphenyl)-2-(3,5-dimethylphenyl)ethyl]-4,5-dihydro-1,3-thiazole-2-amine(known from WO2008/104503),{1′-[(2E)-3-(4-chlorophenyl)prop-2-en-1-yl]-5-fluorospiro[indole-3,4′-piperidine]-1(2H)-yl}(2-chloropyridin-4-yl)methanone(known from WO2003/106457),3-(2,5-dimethylphenyl)-4-hydroxy-8-methoxy-1,8-diazaspiro[4,5]dec-3-en-2-one(known from WO2009/049851),3-(2,5-dimethylphenyl)-8-methoxy-2-oxo-1,8-diazaspiro[4.5]dec-3-en-4-yl-ethylcarbonate (known from WO2009/049851),4-(but-2-yn-1-yloxy)-6-(3,5-dimethylpiperidin-1-yl)-5-fluoropyrimidine(known from WO2004/099160),(2,2,3,3,4,4,5,5-octafluoropentyl)(3,3,3-trifluoropropyl)malononitrile(known from WO2005/063094),(2,2,3,3,4,4,5,5-octafluoropentyl)(3,3,4,4,4-pentafluorobutyl)malononitrile(known from WO2005/063094),8-[2-(cyclopropylmethoxy)-4-(trifluoromethyl)phenoxy]-3-[6-(trifluoromethyl)pyridazin-3-yl]-3-azabicyclo[3.2.1]octane(known from WO2007/040280),2-ethyl-7-methoxy-3-methyl-6-[(2,2,3,3-tetrafluoro-2,3-dihydro-1,4-benzodioxin-6-yl)oxy]-quinolin-4-ylmethylcarbonate (known from JP2008/110953),2-ethyl-7-methoxy-3-methyl-6-[(2,2,3,3-tetrafluoro-2,3-dihydro-1,4-benzodioxin-6-yl)oxy]quinolin-4-ylacetate (known from JP2008/110953), PF1364 (CAS Reg. No. 1204776.60-2)(known from JP2010/018586),5-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazol-3-yl]-2-(1H-1,2,4-triazol-1-yl)benzo-nitrile(known from WO2007/075459),5-[5-(2-chloropyridin-4-yl)-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazol-3-yl]-2-(1H-1,2,4-triazol-1-yl)benzonitrile(known from WO2007/075459),4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazol-3-yl]-2-methyl-N-{2-oxo-2-[(2,2,2-trifluoroethyl)amino]ethyl}benzamide(known from WO2005/085216),4-{[(6-chloropyridin-3-yl)methyl](cyclopropyl)amino}-1,3-oxazol-2(5H)-one,4-{[(6-chloropyridin-3-yl)methyl](2,2-difluoroethyl)amino}-1,3-oxazol-2(5H)-one,4-{[(6-chloropyridin-3-yl)methyl]-(ethyl)amino}-1,3-oxazol-2(5H)-one,4-{[(6-chloropyridin-3-yl)methyl](methyl)amino}-1,3-oxazol-2(5H)-one(all known from WO2010/005692), NNI-0711 (known from WO2002096882),1-acetyl-N-[4-(1,1,1,3,3,3-hexafluoro-2-methoxypropan-2-yl)-3-isobutylphenyl]-N-isobutyryl-3,5-dimethyl-1H-pyrazole-4-carboxamide(known from WO2002096882), methyl2-[2-({[3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazol-5-yl]carbonyl}amino)-5-chloro-3-methylbenzoyl]-2-methyl-hydrazinecarboxylate(known from WO2005/085216), methyl2-[2-({[3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazol-5-yl]carbonyl}amino)-5-cyano-3-methylbenzoyl]-2-ethylhydrazinecarboxylate(known from WO2005/085216), methyl2-[2-({[3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazol-5-yl]carbonyl}amino)-5-cyano-3-methylbenzoyl]-2-methylhydrazinecarboxylate(known from WO2005/085216), methyl2-[3,5-dibromo-2-({[3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazol-5-yl]carbonyl}amino)benzoyl]-1,2-diethylhydrazinecarboxylate(known from WO2005/085214) methyl2-[3,5-dibromo-2-({[3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazol-5-yl]carbonyl}amino)-benzoyl]-2-ethylhydrazinecarboxylate(known from WO2005/085216),(5RS,7RS;5RS,7SR)-1-(6-chloro-3-pyridylmethyl)-1,2,3,5,6,7-hexahydro-7-methyl-8-nitro-5-propoxyimidazo[1,2-a]pyridine(known from WO2007/101369),2-{6-[2-(5-fluoropyridin-3-yl)-1,3-thiazol-5-yl]pyridin-2-yl}pyrimidine(known from WO2010/006713),2-{6-[2-(pyridin-3-yl)-1,3-thiazol-5-yl]pyridin-2-yl}pyrimidine (knownfrom WO2010/006713),1-(3-chloropyridin-2-yl)-N-[4-cyano-2-methyl-6-(methylcarbamoyl)phenyl]-3-{[5-(trifluoromethyl)-1H-tetrazol-1-yl]methyl}-1H-pyrazole-5-carboxamide(known from WO2010/069502),1-(3-chloropyridin-2-yl)-N-[4-cyano-2-methyl-6-(methylcarbamoyl)phenyl]-3-{[5-(trifluoromethyl)-2H-tetrazol-2-yl]methyl}-1H-pyrazole-5-carboxamide(known from WO2010/069502),N-[2-(tert-butylcarbamoyl)-4-cyano-6-methylphenyl]-1-(3-chloropyridin-2-yl)-3-{[5-(trifluoromethyl)-1H-tetrazol-1-yl]methyl}-1H-pyrazole-5-carboxamide(known from WO2010/069502) andN-[2-(tert-butylcarbamoyl)-4-cyano-6-methylphenyl]-1-(3-chloropyridin-2-yl)-3-{[5-(trifluoromethyl)-2H-tetrazol-2-yl]methyl}-1H-pyrazole-5-carboxamide(known from WO2010/069502).

In a preferred embodiment of the invention, a penetrant is additionallyadded to the crop protection compositions to enhance the action. Usefulpenetrants also include, for example, substances which promote theavailability of the compounds of the formula (I) in the spray coating.These include, for example, mineral and vegetable oils. Useful oilsinclude all mineral or vegetable oils—modified or otherwise—which aretypically usable in agrochemical compositions. Examples includesunflower oil, rapeseed oil, olive oil, castor oil, colza oil, cornseedoil, cottonseed oil and soybean oil or the esters of the oils mentioned.Preference is given to rapeseed oil, sunflower oil and their methyl orethyl esters, especially rapeseed oil methyl ester.

The concentration of penetrant in the inventive compositions can bevaried within a wide range. In the case of a formulated crop protectioncomposition, it is generally 1 to 95% by weight, preferably 1 to 55% byweight, more preferably 15-40% by weight. In the ready-to-usecompositions (spray liquors), the concentrations are generally between0.1 and 10 g/l, preferably between 0.5 and 5 g/l.

When used as insecticides, the inventive active ingredients may also bepresent in their commercially available formulations and in the useforms, prepared from these formulations, as a mixture with synergists.Synergists are compounds which enhance the action of the activeingredients, without any need for the synergist added to be activeitself.

When used as insecticides, the inventive active ingredients may also bepresent in their commercially available formulations and in the useforms, prepared from these formulations, as a mixture with inhibitorswhich reduce degradation of the active ingredient after use in theenvironment of the plant, on the surface of parts of plants or in planttissues.

The active ingredient content of the use forms prepared from thecommercially available formulations may vary within wide limits. Theactive ingredient concentration of the application forms may be from0.00000001 to 95% by weight of active ingredient, preferably between0.00001 and 1% by weight.

The compounds are applied in a customary manner appropriate for the useforms.

The good plant compatibility of the active ingredients in theconcentrations needed for control of plant diseases allows treatment ofabove-ground plant parts, of plants and seed, and of the soil.

The inventive treatment of the plants and plant parts with the activeingredients is effected directly or by allowing them to act on thesurroundings, habitat or storage space by the customary treatmentmethods, for example by dipping, spraying, evaporating, fogging,scattering, painting on, injecting, and, in the case of propagationmaterial, especially in the case of seeds, also by applying one or morecoats.

All plants and plant parts can be treated in accordance with theinvention. Plants are understood here to mean all plants and plantpopulations, such as desired and undesired wild plants or crop plants(including naturally occurring crop plants). Crop plants may be plantswhich can be obtained by conventional breeding and optimization methodsor by biotechnological and genetic engineering methods or combinationsof these methods, including the transgenic plants and including theplant varieties which are protectable and non-protectable by plantbreeders' rights. Parts of plants shall be understood to mean allabove-ground and below-ground parts and organs of plants, such as shoot,leaf, flower and root, examples including leaves, needles, stems,trunks, flowers, fruit bodies, fruits and seeds, and also roots, tubersand rhizomes. The plant parts also include harvested material andvegetative and generative propagation material, for example cuttings,tubers, rhizomes, slips and seeds.

Plants which can be treated in accordance with the invention include thefollowing: cotton, flax, grapevine, fruit, vegetables, such as Rosaceaesp. (for example pome fruits such as apples and pears, but also stonefruits such as apricots, cherries, almonds and peaches, and soft fruitssuch as strawberries), Ribesioidae sp., Juglandaceae sp., Betulaceae sp,Anacardceae sp., Fagaceae sp., Moraceae sp., Oleaceae sp., Actinidaceaesp., Lauraceae sp., Musaceae sp. (for example banana plants and bananaplantations), Rubiaceae sp. (for example coffee), Theaceae sp.,Sterculiceae sp., Rutaceae sp. (for example lemons, oranges andgrapefruit); Solanaceae sp. (for example tomatoes), Lilaceae sp,Asteraceae sp. (for example lettuce), Umbelliferae sp., Cruciferae sp.,Chenopodiaceae sp., Cucurbitaceae sp. (for example cucumber), Alliaceaesp. (for example leeks, onions), Papilionaceae sp. (for example peas);major crop plants such as Gramineae sp (for example maize, turf, cerealssuch as wheat, rye, rice, barley, oats, millet and triticale), Poaceaesp (for example sugar cane), Asteroceae sp. (for example sunflower),Brasicaceae sp. (for example white cabbage, red cabbage, broccoli,cauliflower, Brussels sprouts, pak choi, kohlrabi, radishes, and alsooilseed rape, mustard, horseradish and cress), Fabacae sp. (for examplebeans, peanuts), Papilonaceae sp. (for example soya beans), Solanaceaesp. (for example potatoes), Chenopodiaceae sp. (for example sugar beet,fodder beet Swiss chard, beetroot); useful plants and ornamental plantsin gardens and forests; and genetically modified types of each of theseplants.

As already mentioned above, it is possible to treat all plants and theirparts according to the invention. In a preferred embodiment, wild plantspecies and plant cultivars, or those obtained by conventionalbiological breeding methods, such as crossing or protoplast fusion, andalso parts thereof, are treated. In a further preferred embodiment,transgenic plants and plant cultivars obtained by genetic engineering,if appropriate in combination with conventional methods (GeneticallyModified Organisms), and parts thereof are treated. The term “pats” or“parts of plants” or “plant parts” has been explained above. Morepreferably, plants of the plant cultivars which are each commerciallyavailable or in use are treated in accordance with the invention. Plantcultivars are understood to mean plants which have new properties(“traits”) and have been obtained by conventional breeding, bymutagenesis or by recombinant DNA techniques. They can be cultivars,varieties, bio- or genotypes.

The inventive treatment method can be used for the treatment ofgenetically modified organisms (GMOs), for example plants or seeds.Genetically modified plants (or transgenic plants) are plants in which aheterologous gene has been integrated stably into the genome. Theexpression “heterologous gene” essentially means a gene which isprovided or assembled outside the plant and when introduced in thenuclear, chloroplastic or mitochondrial genome gives the transformedplant new or improved agronomic or other properties by expressing aprotein or polypeptide of interest or by downregulating or silencingother gene(s) which are present in the plant (using for exampleantisense technology, cosuppression technology or RNAi technology [RNAinterference]). A heterologous gene present in the genome is also calleda transgene. A transgene that is defined by its specific presence in theplant genome is called a transformation or transgenic event.

Depending on the plant species or plant varieties, their location andgrowth conditions (soils, climate, vegetation period, diet), thetreatment according to the invention may also result in superadditive(“synergistic”) effects. For example, the following effects exceedingthe effects actually to be expected are possible: reduced applicationrates and/or a widening of the activity spectrum and/or an increase inthe activity of the active ingredients and compositions which can beused according to the invention, better plant growth, increasedtolerance to high or low temperatures, increased tolerance to drought orto water or soil salt content, increased flowering performance, easierharvesting, accelerated maturation, higher harvest yields, biggerfruits, larger plant height, greener leaf colour, earlier flowering,higher quality and/or a higher nutritional value of the harvestedproducts, higher sugar concentration within the fruits, better storagestability and/or processability of the harvested products.

At certain application rates, the inventive active ingredients may alsohave a fortifying effect on plants. They are therefore suitable formobilizing the defence system of the plant against attack by unwantedphytopathogenic fungi and/or microorganisms and/or viruses. This may beone of the reasons for the enhanced activity of the inventivecombinations, for example against fungi. Plant-fortifying(resistance-inducing) substances shall be understood to mean, in thepresent context, also those substances or combinations of substanceswhich are capable of stimulating the defence system of plants in such away that, when subsequently inoculated with unwanted phytopathogenicfungi, the plants treated display a substantial degree of resistance tothese unwanted phytopathogenic fungi. The inventive substances cantherefore be used for protection of plants from attack by the pathogensmentioned within a certain period of time after the treatment. Theperiod within which protection is achieved generally extends for from 1to 10 days, preferably 1 to 7 days, after the treatment of the plantswith the active ingredients.

Plants and plant varieties which are preferably treated in accordancewith the invention include all plants which have genetic material whichimparts particularly advantageous, useful traits to these plants(whether obtained by breeding and/or biotechnological means).

Plants and plant varieties which are likewise preferably treated inaccordance with the invention are resistant to one or more biotic stressfactors, i.e. said plants have a better defence against animal andmicrobial pests, such as against nematodes, insects, mites,phytopathogenic fungi, bacteria, viruses and/or viroids.

Plants and plant varieties which may also be treated according to theinvention are those plants which are resistant to one or more abioticstress factors. Abiotic stress conditions may include, for example,drought, cold temperature exposure, heat exposure, osmotic stress,waterlogging increased soil salinity, increased exposure to minerals,exposure to ozone, exposure to strong light, limited availability ofnitrogen nutrients, limited availability of phosphorus nutrients orshade avoidance.

Plants and plant varieties which can likewise be treated in accordancewith the invention are those plants which are characterized by enhancedyield characteristics. Enhanced yield in these plants may be the resultof, for example, improved plant physiology, improved plant growth anddevelopment, such as water use efficiency, water retention efficiency,improved nitrogen use, enhanced carbon assimilation, improvedphotosynthesis, increased germination efficiency and acceleratedmaturation. Yield can also be affected by improved plant architecture(under stress and non-stress conditions), including early flowering,flowering control for hybrid seed production, seedling vigour, plantsize, internode number and distance, root growth, seed size, fruit size,pod size, pod or ear number, seed number per pod or ear, seed mass,enhanced seed filling, reduced seed dispersal, reduced pod dehiscenceand lodging resistance. Further yield traits include seed composition,such as carbohydrate content, protein content, oil content andcomposition, nutritional value, reduction in anti-nutritional compounds,improved processibility and better storage stability.

Plants that may be treated according to the invention are hybrid plantsthat already express the characteristics of heterosis, or hybrid effect,which results in generally higher yield, vigour, health and resistancetowards biotic and abiotic stress factors. Such plants are typicallyproduced by crossing an inbred male-sterile parent line (the femaleparent) with another inbred male-fertile parent line (the male parent).The hybrid seed is typically harvested from the male-sterile plants andsold to growers. Male-sterile plants can sometimes (for example inmaize) be produced by detasseling (i.e. mechanical removal of the malereproductive organs or male flowers); however, it is more typical formale sterility to be the result of genetic determinants in the plantgenome. In that case, and especially when seed is the desired product tobe harvested from the hybrid plants, it is typically beneficial toensure that male fertility in hybrid plants, which contain the geneticdeterminants responsible for male sterility, is fully restored. This canbe accomplished by ensuring that the male parents have appropriatefertility restorer genes which are capable of restoring the malefertility in hybrid plants that contain the genetic determinantsresponsible for male sterility. Genetic determinants for male sterilitymay be located in the cytoplasm. Examples of cytoplasmic male sterility(CMS) were for instance described for Brassica species. However, geneticdeterminants for male sterility can also be located in the nucleargenome. Male-sterile plants can also be obtained by plant biotechnologymethods such as genetic engineering. A particularly useful means ofobtaining male-sterile plants is described in WO 89/10396, in which, forexample, a ribonuclease such as a barnase is selectively expressed inthe tapetum cells in the stamens. Fertility can then be restored byexpression in the tapetum cells of a ribonuclease inhibitor such asbarstar.

Plants or plant varieties (obtained by plant biotechnology methods suchas genetic engineering) which may be treated according to the inventionare herbicide-tolerant plants, i.e. plants made tolerant to one or moregiven herbicides. Such plants can be obtained either by genetictransformation, or by selection of plants containing a mutationimparting such herbicide tolerance.

Herbicide-tolerant plants are, for example, glyphosate-tolerant plants,i.e. plants which have been made tolerant to the herbicide glyphosate orsalts thereof. For example, glyphosate-tolerant plants can be obtainedby transforming the plant with a gene which encodes the enzyme5-enolpyruvylshikimate-3-phosphate synthase (EPSPS). Examples of suchEPSPS genes are the AroA gene (mutant CT7) of the bacterium Salmonellatyphimurium, the CP4 gene of the bacterium Agrobacterium sp., the genesencoding a petunia EPSPS, a tomato EPSPS, or an Eleusine EPSPS. It canalso be a mutated EPSPS. Glyphosate-tolerant plants can also be obtainedby expressing a gene that encodes a glyphosate oxidoreductase enzyme.Glyphosate-tolerant plants can also be obtained by expressing a genethat encodes a glyphosate acetyltransferase enzyme. Glyphosate-tolerantplants can also be obtained by selecting plants containing naturallyoccurring mutations of the abovementioned genes.

Other herbicide-resistant plants are for example plants that have beenmade tolerant to herbicides inhibiting the enzyme glutamine synthase,such as bialaphos, phosphinothricin or glufosinate. Such plants can beobtained by expressing an enzyme detoxifying the herbicide or a mutantglutamine synthase enzyme that is resistant to inhibition. One suchefficient detoxifying enzyme is, for example, an enzyme encoding aphosphinothricin acetyltransferase (such a the bar or pat protein fromStreptomyces species). Plants expressing an exogenous phosphinothricinacetyltransferase have been described.

Further herbicide-tolerant plants are also plants that have been madetolerant to the herbicides inhibiting the enzymehydroxyphenylpyruvatedioxygenase (HPPD).Hydroxyphenylpyruvatedioxygenases are enzymes that catalyse the reactionin which para-hydroxyphenylpyruvate (HPP) is converted to homogentisate.Plants tolerant to HPPD inhibitors can be transformed with a geneencoding a naturally occurring resistant HPPD enzyme, or a gene encodinga mutated HPPD enzyme. Tolerance to HPPD inhibitors can also be obtainedby transforming plants with genes encoding certain enzymes enabling theformation of homogentisate despite the inhibition of the native HPPDenzyme by the HPPD inhibitor. Tolerance of plants to HPPD inhibitors canalso be improved by transforming plants with a gene encoding an enzymeprephenate dehydrogenase in addition to a gene encoding an HPPD-tolerantenzyme.

Further herbicide-resistant plants are plants that have been madetolerant to acetolactate synthase (ALS) inhibitors. The known ALSinhibitors include, for example, sulphonylurea, imidazolinone,trizalopyrimidines, pyrimidinyl oxy(thio)benzoates and/orsulphonylaminocarbonyltriaolinone herbicides. Different mutations in theALS enzyme (also known as acetohydroxy acid synthase, AHAS) are known toconfer tolerance to different herbicides and groups of herbicides. Theproduction of sulphonylurea-tolerant plants and imidazolinone-tolerantplants has been described in the international publication WO1996/033270. Further sulphonylurea- and imidazolinone-tolerant plantshave also been described, for example in WO 2007/024782.

Other plants tolerant to imidazolinone and/or sulphonylurea can beobtained by induced mutagenesis, by selection in cell cultures in thepresence of the herbicide or by mutation breeding.

Plants or plant cultivars (obtained by plant biotechnology methods suchas genetic engineering) which may also be treated according to theinvention are insect-resistant transgenic plants, i.e. plants maderesistant to attack by certain target insects. Such plants can beobtained by genetic transformation, or by selection of plants containinga mutation which imports such insect resistance.

In the present context, the term “insect-resistant transgenic plant”includes any plant containing at least one transgene comprising a codingsequence encoding:

-   1) an insecticidal crystal protein from Bacillus thuringiensis or an    insecticidal portion thereof such as the insecticidal crystal    proteins compiled online at    http://www.lifesci.sussex.ac.uk/Home/Neil_Crickmore/Bt/, or    insecticidal portions thereof, for example proteins of the Cry    protein classes Cry1Ab, Cry1Ac, Cry1F, Cry2Ab, Cry3Ae or Cry3Bb or    insecticidal portions thereof; or-   2) a crystal protein from Bacillus thuringiensis or a portion    thereof which is insecticidal in the presence of a second other    crystal protein than Bacillus thuringiensis or a portion thereof,    such as the binary toxin made up of the Cy34 and Cy35 crystal    proteins; or-   3) a hybrid insecticidal protein comprising parts of two different    insecticidal crystal proteins from Bacillus thuringiensis, such as a    hybrid of the proteins of 1) above or a hybrid of the proteins of 2)    above, for example the Cry1A.105 protein produced by maize event    MON98034 (WO 2007/027777); or-   4) a protein of any one of points 1) to 3) above wherein some,    particularly 1 to 10, amino acids have been replaced by another    amino acid to obtain a higher insecticidal activity to a target    insect species, and/or to expand the range of target insect species    affected, and/or because of changes induced in the encoding DNA    during cloning or transformation, such as the Cry3Bb1 protein in    maize events MON863 or MON88017, or the Cry3A protein in maize event    MIR604; or-   5) an insecticidal secreted protein from Bacillus thuringiensis or    Bacillus cereus, or an insecticidal portion thereof such as the    vegetative insecticidal proteins (VIP) listed at:    http://www.lifesci.sussex.ac.uk/Home/Neil_Crickmore/Bt/vip.html, for    example proteins from the VIP3Aa protein class; or-   6) a secreted protein from Bacillus thuringiensis or Bacillus cereus    which is insecticidal in the presence of a second secreted protein    from Bacillus thuringiensis or B. cereus, such as the binary toxin    made up of the VIP1A and VIP2A proteins;-   7) a hybrid insecticidal protein comprising parts from different    secreted proteins from Bacillus thuringiensis or Bacillus cereus,    such as a hybrid of the proteins in 1) above or a hybrid of the    proteins in 2) above; or-   8) a protein of any one of points 1) to 3) above wherein some,    particularly 1 to 10, amino acids have been replaced by another    amino acid to obtain a higher insecticidal activity to a target    insect species, and/or to expand the range of target insect species    affected, and/or because of changes induced in the encoding DNA    during cloning or transformation (while still encoding an    insecticidal protein), such as the VIP3Aa protein in cotton event    COT 102.

Of course, insect-resistant transgenic plants, as used herein, alsoinclude any plant comprising a combination of genes encoding theproteins of any one of the abovementioned classes 1 to 8. In oneembodiment, an insect-resistant plant contains more than one transgeneencoding a protein of any one of the abovementioned classes 1 to 8, toexpand the range of target insect species affected or to delay insectresistance development to the plants, by using different proteinsinsecticidal to the same target insect species but having a differentmode of action, such as binding to different receptor binding sites inthe insect.

Plants or plant cultivars (obtained by plant biotechnology methods suchas genetic engineering) which may also be treated according to theinvention are tolerant to abiotic stress factors. Such plants can beobtained by genetic transformation, or by selection of plants containinga mutation imparting such stress resistance. Particularly usefulstress-tolerant plants include the following:

-   a. plants which contain a transgene capable of reducing the    expression and/or the activity of the poly(ADP-ribose)polymerase    (PARP) gene in the plant cells or plants;-   b. plants which contain a stress tolerance-enhancing transgene    capable of reducing the expression and/or the activity of the    PARG-encoding genes of the plants or plant cells;-   c. plants which contain a stress tolerance-enhancing transgene    coding for a plant-functional enzyme of the nicotinamide adenine    dinucleotide salvage biosynthesis pathway, including nicotinamidase,    nicatinate phosphoribosyltransferase nicotinic acid mononucleotide    adenyltransferase nicotinamide adenine dinucleotide synthetase or    nicotinamide phosphoribosyltransferase.

Plants or plant cultivars (obtained by plant biotechnology methods suchas genetic engineering) which may also be treated according to theinvention show altered quantity, quality and/or storage stability of theharvested product and/or altered properties of specific ingredients ofthe harvested product such as:

-   1) Transgenic plants which synthesize a modified starch which is    altered with respect to its chemophysical traits, in particular the    amylose content or the amylose/amylopectin ratio, the degree of    branching, the average chain length, the distribution of the side    chains, the viscosity behaviour, the gel resistance, the grain size    and/or grain morphology of the starch in comparison to the    synthesized starch in wild-type plant cells or plants, such that    this modified starch is better suited for certain applications.-   2) Transgenic plants which synthesize non-starch carbohydrate    polymers or which synthesize non-starch carbohydrate polymers with    altered properties in comparison to wild-type plants without genetic    modification. Examples are plants which produce polyfructose,    especially of the inulin and levan type, plants which produce    alpha-1,4-glucans, plants which produce alpha-1,6-branched    alpha-1,4-glucans, and plants producing alternan.-   3) Transgenic plants which produce hyaluronan.

Plants or plant cultivars (obtained by plant biotechnology methods suchas genetic engineering) which may also be treated according to theinvention are plants, such as cotton plants, with altered fibrecharacteristics. Such plants can be obtained by genetic transformation,or by selection of plants containing a mutation imparting such alteredfibre characteristics and include:

-   a) plants, such as cotton plants, which contain an altered form of    cellulose synthase genes;-   b) plants, such as cotton plants, which contain an altered form of    rsw2 or rsw3 homologous nucleic acids;-   c) plants, such as cotton plants, with an increased expression of    sucrose phosphate synthase,-   d) plants, such as cotton plants, with an increased expression of    sucrose synthase;-   e) plants, such as cotton plants, wherein the timing of the    plasmodesmatal gating at the basis of the fibre cell is altered, for    example through downregulation of fibre-selective β-1,3-glucanase;-   f) plants, such as cotton plants, which have fibres with altered    reactivity, for example through the expression of the    N-acetylglucosaminetransferase gene including nodC and chitin    synthase genes.

Plants or plant cultivars (obtained by plant biotechnology methods suchas genetic engineering) which may also be treated according to theinvention are plants, such as oilseed rape or related Brassica plants,with altered oil profile characteristics. Such plants can be obtained bygenetic transformation, or by selection of plants containing a mutationimparting such altered oil characteristics and include:

-   a) plants, such as oilseed rape plants, which produce oil having a    high oleic acid content;-   b) plants, such as oilseed rape plants, which produce oil having a    low linolenic acid content;-   c) plants, such as oilseed rape plants, which produce oil having a    low level of saturated fatty acids.

Particularly useful transgenic plants which may be treated according tothe invention are plants which comprise one or more genes which encodeone or more toxins are the transgenic plants which are sold under thefollowing trade names: YIELD GARD® (for example maize, cotton, soyabeans), KnockOut® (for example maize), BiteGard® (for example maize),BT-Xtra® (for example maize), StarLink® (for example maize), Bollgard®(cotton), Nucotn® (cotton), Nucotn 33B® (cotton), NatureGard® (forexample maize), Protecta® and NewLeaf® (potato). Examples ofherbicide-tolerant plants which should be mentioned are maiz varieties,cotton varieties and soya been varieties which are available under thefollowing trade names: Roundup Ready® (tolerance to glyphosate, forexample maize, cotton, soya beans), Liberty Link® (tolerance tophosphinothricin, for example oilseed rape), IMI® (tolerance toimidazolinone) and SCS® (tolerance to sulphonylurea, for example maize).Herbicide-resistant plants (plants bred in a conventional manner forherbicide tolerance) which should be mentioned include the varietiessold under the Clearfield name (for example maize).

Particularly useful transgenic plants which may be treated according tothe invention are plants containing transformation events, or acombination of transformation events, and that are listed for example inthe databases for various national or regional regulatory agencies (seefor example http://gmoinfo.jrc.it/gmp_browse.aspx andhttp://www.agbios.com/dbase.php).

The plants listed can be treated in accordance with the invention in aparticularly advantageous manner with the compounds of the generalformula (I) and/or the active ingredient mixtures according to theinvention. The preferred ranges stated above for the active ingredientsor mixtures also apply to the treatment of these plants. Particularemphasis is given to the treatment of plants with the compounds ormixtures specifically mentioned in the present text.

The inventive active ingredients act not only against plant, hygiene andstored product pests, but also in the veterinary medicine sector againstanimal parasites (ecto- and endoperasites), such as hard ticks, softticks, mange mites, leaf mites, flies (biting and licking), parasiticfly larvae, lice, hair lice, feather lice and fleas. These parasitesinclude:

From the order of the Anoplurida, for example, Haematopinus spp.,Linognathus spp., Pediculus spp., Phtirus spp. and Solenopotes app.

From the order of the Mallophagida and the suborders Amblycerina andIschnocerina, for example, Trimenopon spp., Menopon spp., Trinoton spp.,Bovicola spp., Werneckiella spp., Lepikentron spp., Damalina spp.,Trichodectes spp., and Felicola spp.

From the order of the Diptera and the suborders Nematocerina andBrachycerina, for example, Aedes spp., Anopheles spp., Culex spp.,Simulium spp., Eusimulium spp., Phlebotomus spp., Lutzomyia spp.,Culicoides spp., Chrysops spp., Hybomitra spp., Atylotus spp., Tabanusspp., Haematopota spp., Philipomyia spp., Braula spp., Musca spp.,Hydrotaea spp., Stomoxys spp., Haematobia spp., Morellia spp., Fanniaspp., Glossina spp., Calliphora spp., Lucilia spp., Chrysomyia spp.,Wohlfahrtia spp., Sarcophaga spp., Ocstrus spp., Hypoderma spp.,Gasterophilus spp., Hippobosca spp., Lipoptena spp. and Melophagus spp.

From the order of the Siphonapterida, for example Pulex spp.,Ctenocephalides spp. (Ctenocephalides canis, Ctenocephalides felis),Xenopsylla spp. and Ceratophyllus spp.

From the order of the Heteropterida, for example, Cimex spp., Triatomaspp., Rhodnius spp. and Panstrongylus spp.

From the order of the Blattarida, for example Blatta orientalis,Periplaneta americana, Blattella germanica and Supella spp.

From the subclass of the Acari (Acarina) and the orders of the Meta- andMesostigmata, for example, Argas spp., Ornithodorus spp., Otobius spp.,Ixodes spp., Amblyomma spp., Boophilus spp., Dermacentor spp.,Haemophysalis spp., Hyalomma spp., Rhipicephalus spp., Dermanyssus spp.,Raillietia spp., Pneumonyssus spp., Sternostoma spp. and Varroa spp.

From the order of the Actinedida (Prostigmata) and Acaridida(Astigmata), for example, Acarapis spp., Cheyletiella spp.,Ornithocheyletia spp., Myobia spp., Psorergates spp., Demodex spp.,Trombicula spp., Listrophorus spp., Acarus spp., Tyrophagus spp.,Caloglyphus spp., Hypodectes spp., Pterolichus spp., Psoroptes spp.,Chorioptes spp., Otodectes spp., Sarcoptes spp., Notoedres spp.,Knemidocoptes spp., Cytodites spp. and Laminosioptes spp.

The inventive active ingredients of the formula (I) are also suitablefor controlling arthropods which attack agricultural livestock, forexample cattle, sheep, goats, horses, pigs, donkeys, camels, buffaloes,rabbits, chickens, turkeys, ducks, geese, honey-bees, other domesticanimals such as, for example, dogs, cats, caged birds, aquarium fish,and experimental animals, for example hamsters, guinea pigs, rats andmice. The control of these arthropods is intended to reduce cases ofdeath and reduced productivity (of meat, milk, wool, hides, eggs, honeyetc.), and so more economic and easier animal husbandry is possible byuse of the inventive active ingredients.

The inventive active ingredients are used in the veterinary sector andin animal husbandry in a known manner, by enteral administration in theform of, for example, tablets, capsules, potions, drenches, granules,pastes, boluses, the feed-through process and suppositories, byparenteral administration, such as, for example, by injection(intramuscular, subcutaneous, intravenous, intraperitoneal and thelike), implants, by nasal administration, by dermal use in the form, forexample, of dipping or bathing, spraying, pouring on and spotting on,washing and powdering, and also with the aid of moulded articlescontaining the active ingredient, such as collars, ear marks, tailmarks, limb bands, halters, marking devices and the like.

When used for livestock, poultry, domestic animals and the like, theactive ingredients of the formula (I) can be used as formulations (forexample powders, emulsions, flowables) comprising the active ingredientsin an amount of 1 to 80% by weight, either directly or after 100 to 10000-fold dilution, or they may be used as a chemical bath.

It has also been found that the inventive compounds have stronginsecticidal action against insects which destroy industrial materials.

Preferred but nonlimiting examples include the following insects:

beetles, such as Hylotrupes bajulus, Chlorophorus pilosis, Anobiumpunctatum, Xestobium rufovillosum, Ptilinus pecticornis, Dendrobiumpertinex, Emobius mollis, Priobium carpini, Lyctus brunnrmeus, Lyctusafricanus, Lyctus planicollis, Lyctus linearis, Lyctus pubescens,Trogoxylon aequale, Minthes rugicollis, Xyleborus spec. Tryptodendronspec., Apate monachus, Bostrychus capucins, Heterobostrychus brunneus,Sinoxylon spec. Dinoderus minutus;dermapterans, such as Sirex juvencus, Urocerus gigas, Urocerus gigastaignus, Urocerus augur,termites, such as Kalotermes flavicollis, Cryptotermes brevis,Heterotermes indicola, Reticulitermes flavipes, Reticulitermessantonensis, Reticulitermes lucifugus, Mastotermes darwiniensis,Zootermopsis nevadensis, Coptotermes formosanus;bristletails, such as Lepisma saccarina.

Industrial materials in the present connection are understood to meaninanimate materials, such as preferably plastics, adhesives, sizes,papers and cards, leather, wood, processed wood products and coatingcompositions.

The ready-to-use compositions may optionally also comprise otherinsecticides, and optionally one or more fungicides.

With respect to possible additional mixing partners, reference is madeto the insecticides and fungicides mentioned above.

At the same time, the inventive compounds can be employed for protectionof objects which come into contact with saltwater or brackish water,especially hulls, screens, nets, buildings, moorings and signallingsystems, against fouling.

In addition, the inventive compounds can be used as antifoulingcompositions, alone or in combinations with other active ingredients.

The active ingredients are also suitable for controlling animal pests inthe domestic sector, in the hygiene sector and in the protection ofstored products, especially insects, arachnids and mites, which arefound in enclosed spaces, for example homes, factory halls, offices,vehicle cabins and the like. They can be used to control these pestsalone or in combination with other active ingredients and auxiliaries indomestic insecticide products. They are effective against sensitive andresistant species, and against all developmental stages. These pestsinclude:

From the order of the Scorpionidea, for example, Buthus occitanus.

From the order of the Acarina, for example, Argas persicus, Argasreflexus, Bryobia spp., Dermanyssus gallina, Glyciphagus domesticus,Ornithodorus moubat, Rhipicephalus sanguineus, Trombicula alfreddugesi,Neutrombicula autumnalis, Dernatophagoides pteronissimus,Dermatophagoides forinae.

From the order of the Araneae, for example, Aviculariidae, Araneidae.

From the order of the Opiliones, for example, Pseudoscorpiones chelifer,Pseudoscorpiones cheiridium, Opiliones phalangium.

From the order of the Isopoda, for example, Oniscus asellus, Porcellioscaber.

From the order of the Diplopoda, for example, Blaniulus guttulatus,Polydesmus spp.

From the order of the Chilopoda, for example, Geophilus spp.

From the order of the Zygentoma, for example, Ctenolepisma spp., Lepismasaccharina, Lepismodes inquilinus.

From the order of the Blattaria, for example, Blatta orientalies,Blattella germanica, Blattella asahinai, Leucophaea maderae, Panchloraspp., Parcoblattas spp., Periplaneta australasiae, Periplanetaamericana, Periplaneta brunnea, Periplaneta fuliginosa, Supellalongipalpa.

From the order of the Saltatoria, for example, Acheta domesticus.

From the order of the Dermaptera, for example, Forficula auricularia.

From the order of the Isoptera, for example, Kalotermes spp.,Reticulitermes spp.

From the order of the Psocoptera, for example, Lepinatus spp.,Liposcelis spp.

From the order of the Coleoptera, for example, Anthrenus spp., Attagenusspp., Dermestes spp., Latheticus oryzae, Necrobia spp., Ptinus spp.,Rhizopertha dominica, Sitophilus granarius, Sitophilus oryzae,Sitophilus zeamais, Stegobium paniceum.

From the order of the Diptera, for example, Aedes aegypti, Aedesalbopictus, Aedes taeniorhynchus, Anopheles spp., Calliphoraerythrocephala, Chrysozona pluvialis, Culex quinquefasciatus, Culexpipiens, Culex tarsalis, Drosophila spp., Fannia canicularis, Muscadomestica, Phlebotomus spp., Sarcophaga camaria, Simulium spp., Stomoxyscalcitrans, Tipula paludosa.

From the order of the Lepidoptera, for example, Achroia grisella,Galleria mellonella, Plodia interpunctella, Tinea cloacella, Tineapellionella, Tineola bisselliella.

From the order of the Siphonaptera, for example, Ctenocephalides canis,Ctenocephalides felis, Pulex irritans, Tungs penetrans, Xenopsyllacheopis.

From the order of the Hymenoptera, for example, Camponotus herculeanus,Lasius fuliginosus, Lasius niger, Lasius umbratus, Monomorium pharaonis,Paravespula spp., Tetramorium cacspitum.

From the order of the Anoplura, for example, Pediculus humanus capitis,Pediculus humanus corporis, Pemphigus spp., Phylloera vastatrix,Phthirus pubis.

From the order of the Heteroptera, for example, Cimex hemipterus, Cimexlectularius, Rhodinus prolixus, Triatoma infestans.

In the field of domestic insecticides, they are used alone or incombination with other suitable active ingredients, such as phosphoricesters, carbamates, pyrethroids, neonicotinoids, growth regulators oractive ingredients from other known classes of insecticides.

They are employed in aerosols, unpressurized spray products, for examplepump and atomizer sprays, automatic fogging systems, foggers, foams,gels, evaporator products with evaporator tablets made of cellulose orplastic, liquid evaporators, gel and membrane evaporators,propeller-driven evaporators, energy-free or passive evaporationsystems, moth papers, moth bags and moth gels, as granules or dusts, inbaits for spreading or in bait stations.

PREPARATION EXAMPLES Example AN-(6-[1-(Pyridin-3-yl)-1H-pyrazol-4-yl]pyridin-2-yl)methanesulphonamideStage 1: 3-(4-Bromopyrazol-1-yl)pyridine

3-Pyrazol-1-ylpyridine (500 mg, 3.44 mmol) was dissolved in acetonitrile(15 ml), and ammonium cerium(IV) nitrate (944 mg, 1.72 mmol) was added(slightly exothermic). N-Bromosuccinimide (736 mg, 4.13 mmol) was addedin portions (slightly exothermic) and the mixture was stirred at roomtemperature for 30 minutes (min) and then heated under reflux for 3hours (h). After the mixture had cooled, ethyl acetate was added. Theorganic phase was washed with water, washed with a sodium sulphatesolution and then dried over magnesium sulphate. The solvent was removedon a rotary evaporator under reduced pressure.

Yield: 750 mg (93% of theory), log P (HCOOH) 1.56, [M⁺+1] 224.0

¹H NMR (d₆-DMSO): 7.54 (m, 1H), 7.90 (s, 1H), 8.20 (m, 1H), 8.55 (m,1H), 8.79 (s, 1H), 9.06 (m, 1H).

Stage 2:3-[4-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)pyrazol-1-yl]pyridine

Under argon, 3-(4-bromopyrazol-1-yl)pyridine (1.00 g, 4.46 mmol),1,1′-bis(diphenylphosphino)-ferrocene (dppf) (74 mg, 0.13 mmol),palladium dichloride-dppf (109 mg, 0.13 mmol), potassium acetate (1.31g, 13.3 mmol) and pinacolatodiborane (1.19 g, 4.68 mmol) were added todioxane (11 ml). The mixture was heated under reflux for 24 h and thencooled. The solvent was removed on a rotary evaporator under reducedpressure, dichloromethane (100 ml) and water (100 ml) were added to theresidue, and the solids formed were filtered off with suction anddiscarded. The filtrate was extracted with dichloromethane and theorganic phase was dried over magnesium sulphate. The solvent was removedon a rotary evaporator under reduced pressure and the residue waschromatographed (ethyl acetate, cyclohexane).

Yield: 680 mg (55% of theory), log P (HCOOH) 2.19, [M⁺+1] 272.2

¹H NMR (d₆-DMSO): 1.30 (s, 12H), 7.51 (m, 1H), 7.90 (s, 1H), 8.25 (m,1H), 8.51 (m, 1H), 8.73 (s, 1H), 9.12 (m, 1H).

Stage 3: 6-[1-(Pyridin-3-yl)-1H-pyrazol-4-yl]pyridine-2-amine

Under argon, 3.17 g (11.7 mmol) of3-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl]pyridine,2.02 g (11.7 mmol) of 6-bromopyridine-2-amine and 945 mg (817 μmol) oftetrakis(triphenylphosphine)palladium were added to a mixture, degassedby means of argon, of 23.3 ml of 2 M sodium carbonate solution in waterand 63.3 ml of acetonitrile. The reaction mixture was heated to 75° C.for 18 hours, diluted with acetonitrile after cooling, dried over MgSO,filtered and concentrated. The crude product thus obtained was purifiedby chromatography (acetonitrile/acetone).

Yield 1.76 g (71% of theory)

HPLC-MS: log P (HCOOH): 0.30; mass (m/z): 238.1 (M+H)⁺

¹H NMR (d6-DMSO): 5.88 (s, 2H), 6.35 (d, 1H), 6.93 (d, 1H), 7.42 (t,1H), 7.58 (dd, 1H), 8.22 (s, 1H), 8.28 (m, 1H), 8.54 (dd, 1H), 8.97 (s,1H), 9.15 ppm (d, 1H).

Stage 4:N-{6-[1-(Pyridin-3-yl)-1H-pyrazol-4-yl]pyridin-2-yl}methanesulphonamide

146 mg (585 μmol) of6-[1-(pyridin-3-yl)-1H-pyrazol-4-yl]pyridine-2-amine and 54.0 μl (701μmol) of N-methylmorpholine were initially charged in 10 ml ofdichloromethane, and methanesulphonyl chloride was added at roomtemperature. The mixture was stirred overnight and the reaction mixturewas filtered through silica gel (eluent: ethyl acetate). Afterconcentration, the crude product was purified by chromatography(dichloromethane/methanol).

Yield: 50 mg (27% of theory); HPLC-MS: log P (HCOOH): 1.26; mass (m/z):316.0 (M+H)⁺;

¹H NMR (d6-DMSO): 6.82 (d, 1H), 7.45 (d, 1H), 7.59 (dd, 1H), 7.78 (t,1H), 8.30 (m, 2H), 8.57 (dd, 1H), 9.09 (s, 1H), 9.17 (d, 1H), 10.55 ppm(s, 1H).

Example B6-[2-(5-Fluoropyridin-3-yl)-1,3-thiazol-5-yl]-N-[(trifluoromethyl)sulphonyl]-pyridine-2-carboxamideStage 1: 3-Fluoro-5-(1,3-thiazol-2-yl)pyridine

2.0 g (8.97 mmol) of the pyridyl boric ester, 1.47 g (8.97 mmol) of the2-bromothiazole, 197 mg (0.27 mmol) ofbis(diphenylphosphino)ferrocenepalladium(II) chloride and 3.72 g (26.9mmol) of potassium carbonate were stirred under argon in 40 ml ofdimethoxyethane at 80° C. for 16 h.

For workup, the mixture was concentrated and purified by means of columnchromatography on silica gel (eluent: cyclohexane/ethyl acetate).

Yield: 778 mg (48% of theory)

HPLC-MS: log P (HCOOH): 1.48; mass (m/z): 180.9 (M+H)⁺;

¹H NMR (d6-DMSO): 7.95 (m, 1H), 8.04 (m, 1H), 8.24 (m, 1H), 8.69 (m,1H), 9.04 (m, 1H) ppm.

Stage 2: Methyl6-[2-(5-fluoropyridin-3-yl)-1,3-thiazol-5-yl]pyridine-2-carboxylate

748 mg (4.15 mmol) of the fluoropyridylthiazole, 897 mg (4.15 mmol) ofthe bromopyridine, 62 mg (0.13 mmol) of dihydrogen dichlorobis(di-t-butylphosphinito-kP)palladate(2−)(dichloro{bis[di-tert-butyl(hydroxy)phosphoranyl]}palladium, POPd, fromCombiPhos, USA) and 1.147 g (8.3 mmol) of potassium carbonate werestirred in 10 ml of dimethylformamide under argon at 120° C. for 16 h.

For workup, the mixture was concentrated and purified by means of columnchromatography on silica gel (eluent: cyclohexane/ethyl acetate).

Yield: 615 mg (47% of theory)

HPLC-MS: log P (HCOOH): 2.37; mass (m/z): 316.0 (M+H)⁺;

¹H NMR (d6-DMSO): 3.93 (s, 3H), 8.03 (m, 1H), 8.14 (m, 1H), 8.36 (m,2H), 8.73 (m, 1H), 8.80 (m, 1H), 9.12 (m, 1H) ppm.

Stage 3:6-[2-(5-Fluoropyridin-3-yl)-1,3-thiazol-5-yl]pyridine-2-carboxylic acid

570 mg (1.81 mmol) of the methyl pyridylcarboxylate were dissolved in amixture of 25 ml of tetrahydrofuran and 8 ml of water, a solution of 152mg (3.62 mmol) of lithium hydroxide monohydrate in 17 ml of water wasadded and the mixture was stirred at room temperature for 16 h.

For workup, the mixture was concentrated and partitioned between waterand methyl t-butyl ether, the aqueous phase was acidified with 1Nhydrochloric acid, and the precipitated solid was filtered off withsuction and dried.

Yield: 556 mg (91% of theory)

HPLC-MS: log P (HCOOH): 1.72; mass (m/z): 302.1 (M+H)⁺;

¹H NMR (d6-DMSO): 8.00 (m, 1H), 8.10 (m, 1H), 832 (m, 2H), 8.72 (m, 1H),8.78 (m, 1H), 9.10 (m, 1H), 13.5 (br) ppm.

Stage 4:6-[2-(5-Fluoropyridin-3-yl)-1,3-thiazol-5-yl]-N-[(trifluoromethyl)sulphonyl]pyridine-2-carboxamide

100 mg (0.33 mmol) of the pyridylcarboxylic acid were initially chargedin 5 ml of tetrahydrofuran, 81 mg (0.50 mmol) of carbonyldiimidazolewere added and the mixture was boiled at reflux for 1 h. After coolingto room temperature, 74 mg (0.50 mmol) of trifluoromethanesulphonamidewere added, the mixture was stirred for 10 min, then 76 mg (0.50 mmol)of diazabicycloundecene (DBU) were added and the mixture was stirred atroom temperature for 16 h.

For workup, the mixture was concentrated and purified by means of columnchromatography on silica gel (eluent: dichloromethane/methanol).

Yield: 28 mg (20% of theory)

HPLC-MS: log P (HCOOH): 1.86; mass (m/z): 433.0 (M+H)⁺;

¹H NMR (d6-DMSO): 7.60 (m, 1H), 7.88 (m, 1H), 7.96 (m, 1H), 8.12 (m,1H), 8.30 (m, 1H), 8.70 (m, 1H), 8.89 (m, 1H), 9.10 (m, 1H) ppm.

Example C6-[5-(5-Fluoropyridin-3-yl)-1,3,4-thiadiazol-2-yl]-N-(methylsulphonyl)pyridine-2-carboxamide

200 mg (0.64 mmol) of the lithium salt and 1.01 g (7.78 mmol) ofdiisopropylethylamine were initially charged in 5 ml of acetonitrile,198 mg (0.77 mmol) of bis(2-oxo-3-oxazolidinyl)-phosphinyl chloride(BOP-CI) were added, the mixture was stirred for 20 min, 185 mg (1.94mmol) of methanesulphonamide and 99 mg (0.64 mmol) ofdiazabicycloundecene (DBU) were added and the mixture was stirred atroom temperature for 16 h.

For workup, the mixture was concentrated and partitioned between waterand ethyl acetate, and the organic phase was dried and concentrated. Thefurther purification was effected by means of column chromatography onsilica gel (eluent: dichloromethane/methanol) and then on RP18 silicagel (eluent: water/acetonitrile).

Yield: 37 mg (15% of theory)

HPLC-MS: log P (HCOOH): 1.79; mass (m/z): 380.1 (M+H)⁺;

1H NMR (d6-DMSO): 3.40 (s, 3H), 8.22 (m, 1H), 8.30 (m, 1H), 8.48 (m,1H), 8.59 (m, 1H), 8.82 (m, 1H), 9.18 (m, 1H), 12.1 (br) ppm.

Example D6-[1-(5-Fluoropyridin-3-yl)-1H-pyrazol-4-yl]-N-(methylsulphonyl)pyridine-2-carboxamideStage 1: 6-Bromo-N-(methylsulphonyl)pyridine-2-carboxamide

5.40 g (26.7 mmol) of 6-bromo-2-pyridinecarboxylic acid were initiallycharged in 150 ml of tetrahydrofuran, 6.51 g (40.0 mmol) ofcarbonyldiimidazole were added and the mixture was boiled at reflux for1 h. After cooling to room temperature, 3.81 g (40.0 mmol) ofmethanesulphonamide were added, the mixture was stirred for 10 min, then6.10 g (40 mmol) of diazabicycloundecene (DBU) were added and themixture was stirred at room temperature for 16 h.

For workup, the mixture was concentrated and purified by means of columnchromatography on silica gel (eluent: dichloromethane/methanol).

Yield: 5.10 g (69% of theory)

HPLC-MS: log P (HCOOH): 1.21; mass (m/z): 281.0 (M+H)⁺;

¹H NMR (d6-DMSO): 3.37 (s, 3H), 7.95 (m, 2H), 8.06 (m, 1H) ppm.

Stage 2: N-(Methylsulphonyl)-6-(1H-pyrazol-4-yl)pyridine-2-carboxamide

285 mg (1.47 mmol) of the 4-pyrazoleboronic ester, 410 mg (1.47 mmol) ofthe bromopyridine, 32 mg (0.04 mmol) ofbis(diphenylphosphino)ferrocenepalladium(II) chloride and 467 mg (4.41mmol) of potassium carbonate were stirred in 10 ml of dimethoxyethaneunder argon at 80° C. for 16 h.

For workup, the mixture was concentrated and purified by means of columnchromatography on silica gel (eluent: cyclohexane/ethyl acetate).

Yield: 145 mg (37% of theory)

HPLC-MS: log P (HCOOH): 0.91; mass (m/z): 267.0 (M+H)⁺

Stage 3:6-[1-(5-Fluoropyridin-3-yl)-1H-pyrazol-4-yl]-N-(methylsulphonyl)pyridine-2-carboxamide

43 mg (0.37 mmol) of 3,5-difluoropyridine, 99 mg (0.37 mg) of thepyrazolylpyridine, 6 mg (0.01 mmol) of dihydrogen dichlorobis(di-t-butylphosphinito-kP)palladate(2−) (POPd, from CombiPhos, USA)and 102 mg (0.74 mmol) of potassium carbonate were stirred in 5 ml ofdimethylformamide under argon at 120° C. for 12 h.

For workup, the mixture was concentrated and purified by means of columnchromatography on silica gel (eluent: dichloromethane/methanol).

Yield: 35 mg (26% of theory)

HPLC-MS: log P (HCOOH): 1.98; mass (m/z): 362.1 (M+H)*;

¹H NMR (d6-DMSO): 3.40 (s, 3H), 7.98 (m, 1H), 8.08 (m, 2H), 8.2 (m, 1H),8.58 (m, 1H), 8.70 (m, 1H), 9.08 (m, 1H), 9.40 (m, 1H) ppm.

Example EN-({6-[2-(Pyridin-3-yl)-1,3-thiazol-5-yl]pyridin-2-yl}sulphonyl)acetamideStage 1: N-[(6-Bromopyridin-2-yl)sulphonyl]acetamide

6-Bromopyridine-2-sulphonamide (0.5 g, 2.11 mmol, prepared by themethods described in WO2005/058299) and potassium carbonate (2.92 g,21.1 mmol) were initially charged in acetonitrile (10 ml). While coolingwith ice, acetyl chloride (1.16 g, 14.8 mmol) was added dropwise and thereaction mixture was stirred at room temperature for 16 h. The solventwas removed under reduced pressure, and the residue was taken up inwater and acidified with dilute hydrochloric acid solution. It wasextracted with ethyl acetate and the solvent was removed under reducedpressure. This gave 0.54 g (85% of theory) ofN-[(6-bromopyridin-2-yl)sulphonyl]-acetamide.

HPLC-MS: Log P (HCOOH): 0.95; mass (m/z): 278.9 (M+H)⁺;

¹H NMR (d6-DMSO): 1.99 (s, 3H), 7.99-8.01 (m, 1H), 8.08 (t, 1H),8.11-8.13 (m, 1H), 12.48 (s, 1H) ppm.

Stage 2:N-({6-[2-(Pyridin-3-yl)-1,3-thiazol-5-yl]pyridin-2-yl}sulphonyl)acetamide

N-[(6-Bromopyridin-2-yl)sulphonyl]acetamide (0.112 g, 0.4 mmol),3-(1,3-thiazol-2-yl)pyridine (0.065 g, 0.4 mmol, prepared by the methodsdescribed in WO 2010/006713),dichloro{bis[di-tert-butyl(hydroxy)phosphoranyl]}palladium (0.006 g,0.012 mmol) and caesium carbonate (0.26 g, 0.8 mmol) were stirred in 10ml of N,N-dimethylformamide at 120° C. under argon for 16 h. Aftercooling, the solvent was removed under reduced pressure and the residuewas chromatographed (silica gel, dichloromethane/methanol eluent). Thisgave 0.024 g (15% of theory) ofN-({6-[2-(pyridin-3-yl)-1,3-thiazol-5-yl]pyridin-2-yl}sulphonyl)acetamide.

HPLC-MS: Log P (HCOOH): 1.30; mass (m/z): 361.0 (M+H)⁺;

¹H NMR (d6-DMSO): 2.03 (s, 3H), 7.61 (m, 1H), 8.02 (m, 1H), 8.13 (m,1H), 830 (m, 1H), 8.41 (m, 1H), 8.71 (m, 1H), 8.91 (m, 1H), 9.20 (m, 1H)ppm.

Example FN-({6-[1-(Pyridin-3-yl)-1H-pyrazol-4-yl]pyridin-2-yl}sulphonyl)acetamideStage 1: 6-[(Pyridin-3-yl)-1H-pyrazol-4-yl]pyridine-2-sulphonamide

Under argon,3-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl]pyridine(0.2 g, 0.74 mmol, prepared by the methods described in WO 2011/045224),6-bromopyridin-2-sulphonamide (0.175 g, 0.74 mmol) andtetrakis(triphenylphosphine)palladium (0.025 g, 0.022 mmol) were addedto a mixture, degassed by means of argon, of sodium carbonate solutionin water (2.9 ml, 2 M/L) and acetonitrile (4 ml). The reaction mixturewas stirred at 70° C. for 18 h. After cooling, the reaction mixture waspoured onto water and the precipitated crystals were filtered off withsuction. They were subsequently stirred with diethyl ether and filteredoff with suction. This gave 0.23 g (97% of theory) of6-[1-(pyridin-3-yl)-1H-pyrazol-4-yl]pyridine-2-sulphonamide.

HPLC-MS: Log P (HCOOH): 0.99; mass (m/z): 302.1 (M+H)⁺

¹H NMR (d6-DMSO): 7.43 (s, 2H), 7.60-7.63 (m, 1H), 7.76 (d, 1H), 8.00(d, 1H), 8.11 (t, 1H), 8.28-8.31 (m, 1H), 8.53 (s, 1H), 8.58-8.60 (m,1H), 9.16-9.17 (m, 1H), 9.33 (s, 1H) ppm

Stage 2:N-({6-[1-(Pyridin-3-yl)-1H-pyrazol-4-yl]pyridin-2-yl}sulphonyl)acetamide

6-[1-(Pyridin-3-yl)-1H-pyrazol-4-yl]pyridin-2-sulphonamide (0.15 g, 0.44mmol) was initially charged in acetonitrile (1.5 ml) under argon, andsodium hydride (0.026 g, 0.66 mmol, 60%) was added in portions. Thereaction mixture was stirred at room temperature for 1 h, then acetylchloride (0.052 g, 0.66 mmol) was added dropwise. The reaction mixturewas stirred at 82° C. for 33 h and, after cooling, the solvent wasremoved under reduced pressure. The residue was taken up in saturatedsodium hydrogencarbonate solution, dichloromethane was added and theprecipitated solid was filtered off. The phases of the filtrate wereseparated; the aqueous phase was adjusted to pH 3 with hydrochloric acidand left to stand for 16 h. The precipitated crystals were filtered offwith suction. Yield 0.02 g (12% of theory) ofN-({6-[1-(pyridin-3-yl)-1H-pyrazol-4-yl-pyridin-2-yl}sulphonyl)acetamide.

HPLC-MS: Log P (HCOOH): 1.17; mass (m/z): 344.1 (M+H)⁺

¹H NMR (d6-DMSO): 2.03 (s, 3H), 7.60-7.64 (m, 1H), 7.92-7.94 (m, 1H),8.08-8.10 (m, 1H), 8.17-8.20 (m, 1H), 8.29-8.31 (m, 1H), 8.37 (s, 1H),8.59-8.60 (m, 1H), 9.16-9.17 (m. 1H), 9.26 (s, 1H), 12.31 (s, 1H) ppm

Example GN-(Methylsulphonyl)-2-[1-(pyridin-3-yl)-1H-pyrazol-4-yl]-1,3-thiazole-4-carboxamideStage 1: 2-Bromo-N-(methylsulphonyl)-1,3-thiazole-4-carboxamide

2-Bromo-1,3-thiazole-4-carboxylic acid (0.8 g, 3.85 mmol) was initiallycharged in tetrahydrofuran (10 ml). N,N′-Carbonyldiimidazole (0.94 g.5.77 mmol) was added and the reaction mixture was heated under refluxfor 1 h. Methanesulphonamide (0.55 g, 5.77 mmol) was added and, after 10min, 1,8-diazabicyclo[5.4.0]undec-7-ene (0.88 g, 5.77 mmol). Thereaction mixture was stirred at room temperature for 16 h and then thesolvent was removed under reduced pressure. The residue was taken up inwater and acidified with hydrochloric acid. The precipitated product wasfiltered off with suction. The aqueous phase was extracted withdichloromethane; the organic phase was dried over sodium sulphate andfiltered, and the solvent was removed under reduced pressure. This gavea total of 1.0 g (89% of theory) of2-bromo-N-(methylsulphonyl)-1,3-thiazole-4-carboxamide.

HPLC-MS: Log P (HCOOH): 0.83; mass (m/z): 284.9 (M+H)⁺;

¹H NMR (d6-DMSO): 3.33 (s, 3H), 8.61 (s, 1H), 12.00 (s, 1H)

Stage 2:N-(Methylsulphonyl)-2-[1-(pyridin-3-yl)-1H-pyrazol-4-yl]-1,3-thiazole-4-carboxamide

Under argon,3-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl]pyridine(0.1 g, 0.37 mmol),2-bromo-N-(methylsulphonyl-1,3-thiazole-4-carboxamide (0.105 g, 0.37mmol) and tetrakis(triphenylphosphine)palladium (0.013 g, 0.011 mmol)were added to a mixture, degassed by means of argon, of sodium carbonatesolution in water (1.5 ml, 2 M/L) and acetonitrile (3.8 ml). Thereaction mixture was stirred at 70° C. for 16 h. After cooling, thereaction mixture was poured onto water and extracted withdichloromethane. The organic phase was dried over sodium sulphate andthe solvent was removed under reduced pressure. The residue wassubsequently stirred with diethyl ether and filtered off with suction.This gave 0.23 g (97% of theory) of6-[1-(pyridin-3-yl)-1H-pyrazol-4-yl]pyridine-2-sulphonamide.

HPLC-MS: Log P (HCOOH): 1.25; mass (m/z): 350.1 (M+H)⁺

¹H NMR (d6-DMSO): 3.38 (S, 3H), 7.48-7.49 (m, 1H), 8.32-8.35 (m, 1H),8.45 (s, 1H), 8.56 (s, 1H), 8.59-8.60 (m, 1H), 9.19-9.20 (m, 1H), 9.34(s, 1H) ppm

Example H4-[1-(5-Fluoropyridin-3-yl)-1H-pyrazol-4-yl]-N-(methylsulphonyl)-1,3-thiazole-2-carboxamideStage 1: 4-Bromo-N-(methylsulphonyl)-1,3-thiazole-2-carboxamide

4-Bromo-1,3-thiazole-2-carboxylic acid (1.0 g, 4.8 mmol) were initiallycharged in tetrahydrofuran (10 ml). N,N′-Carbonyldiimidazole (1.17 g,7.2 mmol) was added and the reaction mixture was heated under reflux for1 h. Methanesulphonamide (0.69 g, 7.2 mmol) was added and, after 10 min,1,8-diazabicyclo[5.4.0]undec-7-ene (1.10 g, 7.2 mmol). The reactionmixture was stirred at room temperature for 16 h and then the solventwas removed under reduced pressure. The residue was taken up in waterand acidified with hydrochloric acid. The precipitated product wasfiltered off with suction. This gave 1.18 g (84% of theory) of4-bromo-N-(methylsulphonyl)-1,3-thiazole-2-carboxamide.

HPLC-MS: Log P (HCOOH): 0.63; mass (m/z): 284.9 (M+H)⁺;

¹H NMR (d6-DMSO): 3.31 (s, 3H), 8.31 (s, 1H)

Stage 2:4-[1-(5-Fluoropyridin-3-yl)-1H-pyrazol-4-yl]-N-(methylsulphonyl)-1,3-thiazole-2-carboxamide

Under argon,3-fluoro-5-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl]pyridine(0.2 g, 0.69 mmol, prepared by the methods described in WO 2011/045224),2-bromo-N-(methylsulphonyl)-1,3-thiazole-4-carboxamide (0.2 g, 0.69mmol) and tetrakis-(triphenylphosphine)palladium (0.024 g, 0.021 mmol)were added to a mixture, degassed by means of argon, of sodium carbonatesolution in water (2.8 ml, 2 M/L) and acetonitrile (9.4 ml). Thereaction mixture was stirred at 70° C. for 16 h. After cooling, thereaction mixture was poured onto water and extracted withdichloromethane. The aqueous phase was acidified with hydrochloric acidand the precipitated solid was filtered off with suction. The crudeproduct was chromatographed with ethyl acetate/2-propenol on silica gel.This gave 0.21 g (8% of theory) of4-[1-(5-fluoropyridin-3-yl)-1H-pyrazol-4-yl]-N-(methylsulphonyl)-1,3-thiazole-2-carboxamide.

HPLC-MS: Log P (HCOOH): 1.68; mass (m/z): 368.1 (M+H)⁺

¹H NMR (d6-DMSO): 2.99 (s, 3H), 7.96 (s, 1H), 8.33 (s, 1H), 8.34 (s,1H), 8.55-8.57 (m, 1H), 9.10 (s, 1H), 9.12 (s, 1H) ppm

Example I3-[2-(5-Fluoropyridin-3-yl)-4-methyl-1,3-thiazol-5-yl]-1-methyl-N-(methyl-sulphonyl)-1H-pyrazole-5-carboxamideStage 1: Ethyl4-[2-(5-fluoropyridin-3-yl)-4-methyl-1,3-thiazol-5-yl]-2,4-dioxobutanoate

Under argon, lithium bis(trimethylsilyl)amide (21 ml, 1 M/L intetrahydrofuran) was initially charged in tetrahydrofuran (150 ml). At−78° C., 1-[2-(5-fluoropyridin-3-yl)-4-methyl-1,3-thiazol-5-yl]ethanone(5.0 g, 21 mmol, prepared analogously to Biorg. & Med. Chem. Lett 1056(2007) and 2828 (2010)) dissolved in diethyl ether was slowly addeddropwise and the reaction mixture was stirred for 2 h. Diethyl oxalate(3.1 g, 21 mmol) dissolved in ether was added dropwise and the reactionmixture was stirred at room temperature for 16 h. Subsequently,potassium hydrogensulphate solution (5%) was added and the mixture wasextracted repeatedly with ethyl acetate. The combined organic phaseswere dried and the solvent was removed under reduced pressure. This gave7.1 g (99% of theory) of ethyl4-[2-(5-fluoropyridin-3-yl)-4-methyl-1,3-thiazol-5-yl]-2,4-dioxobutanoate.

HPLC-MS: Log P (HCOOH): 3.37; mass (m/z): 337.1 (M+H)⁺

¹H NMR (d6-DMSO): 1.31 (t, 3H), 2.79 (s, 3H), 4.31-4.32 (m, 2H), 6.71(bs, 2H), 8.33 (d, 1H), 8.77 (s, 1H), 9.10 (s, 1H) ppm

Stage 2: Ethyl3-[2-(5-fluoropyridin-3-yl)-4-methyl-1,3-thiazol-5-yl]-1-methyl-1H-pyrazole-5-carboxylate

Ethyl4-[2-(5-fluoropyridin-3-yl)-4-methyl-1,3-thiazol-5-yl]-2,4-dioxobutanoate(6.9 g, 20.5 mmol) and methylhydrazine (0.65 g, 20.5 mmol) were heatedin ethanol (250 ml) under reflux for 2 b. The product formed wasfiltered off with suction and the solvent of the filtrate was removedunder reduced pressure. The residue was chromatographed on silica gel(cyclohexane/ethyl acetate eluent). This gave a total of 1.24 g (17% oftheory) of ethyl3-[2-(5-fluoropyridin-3-yl)-4-methyl-1,3-thiazol-5-yl]-1-methyl-1H-pyrazole-5-carboxylate.As a by-product, 4.8 g (67% of theory) of ethyl5-[2-(5-fluoropyridin-3-yl)-4-methyl-1,3-thiazol-5-yl]-1-methyl-1H-pyrazole-3-carboxylatewere obtained.

HPLC-MS: Log P (HCOOH): 3.70; mass (m/z): 347.0 (M+H)⁺

¹H NMR (d6-DMSO): 1.35 (t, 3H), 2.63 (s, 3H), 4.15 (s, 3H), 4.35 (q,2H), 7.17 (s, 1H), 8.19-8.22 (m, 1H), 8.68-8.69 (m, 1H), 9.00-9.01 (m,1H) ppm

Stage 3:3-[2-(5-Fluoropyridin-3-yl)-4-methyl-1,3-thiazol-5-yl]-1-methyl-1H-pyrazole-5-carboxylicacid

Ethyl3-[2-(5-fluoropyridin-3-yl)-4-methyl-1,3-thiazol-5-yl]-1-methyl-1H-pyrazole-5-carboxylate(1.1 g. 3.1 mmol) was dissolved in tetrahydrofuran (200 ml) and water(100 ml), and lithium hydroxide monohydrate (0.26 g, 6.2 mmol) dissolvedin water (100 ml) was added. The reaction mixture was stirred at roomtemperature for 16 h, then neutralized with hydrochloric acid, and thesolvent was removed under reduced pressure. The precipitated solid wasfiltered off with suction. This gave 0.96 g (94% of theory) of3-[2-(5-fluoropyridin-3-yl)-4-methyl-1,3-thiazol-5-yl]-1-methyl-1H-pyrazole-5-carboxylicacid.

HPLC-MS: Log P (HCOOH): 2.05; mass (m/z): 319.0 (M+H)⁺

¹H NMR (d6-DMSO): 2.62 (s, 3H), 4.14 (s, 3H), 7.13 (s, 1H), 8.18-8.22(m, 1H), 8.68-8.69 (m, 1H), 9.00-9.01 (m, 1H) ppm

Stage 4:3-[2-(5-Fluoropyridin-3-yl)-4-methyl-1,3-thiazol-5-yl]-1-methyl-N-(methylsulphonyl)-1H-pyrazole-5-carboxamide

3-[2-(5-Fluoropyridin-3-yl)-4-methyl-1,3-thiazol-5-yl]-1-methyl-1H-pyrazole-5-carboxylicacid (0.08 g, 0.25 mmol) and methanesulphonamide (0.024 g, 0.25 mmol)were initially charged in ice-cooled dichloromethane (10 ml).4-Dimethylaminopyridine (0.006 g, 0.05 mmol) andN-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (0.053 g.0.275 mmol) were added. The reaction mixture was stirred at 0° C. for 2h and then at room temperature for 16 h. The solvent was removed underreduced pressure and the residue was chromatographed on silica gel(dichloromethane/ethyl acetate eluent). This gave 0.074 g (72% oftheory) of3-[2-(5-fluoropyridin-3-yl)-4-methyl-1,3-thiazol-5-yl]-1-methyl-N-(methylsulphonyl)-1H-pyrazole-5-carboxamide.

HPLC-MS: Log P (HCOOH): 2.04; mass (m/z): 396.0 (M+H)⁺

¹H NMR (d6-DMSO): 2.55 (s, 3H), 3.40 (s, 3H), 4.12 (s, 3H), 7.68 (m,1H), 8.12 (m, 1H), 8.69 (m, 1H), 9.01 (m, 1H) ppm

Example J Methyl6-[2-(5-Fluoropyridin-3-yl)-1,3-thiazol-5-yl]pyridine-2-carboximidoateStage 1:6-[2-(5-Fluoropyridin-3-yl)-1,3-thiazol-5-yl]pyridine-2-carbonitrile

Under argon, 3-fluoro-5-(1,3-thiazol-2-yl)pyridine (0.99 g, 5.47 mmol)and 6-bromopyridin-2-carbonitrile (1.0 g, 5.47 mmol) were initiallycharged in DMF (15 ml). After 10 min, at room temperature,tris(2-methylphenyl)phosphine (0.13 g. 0.23 mmol) and palladium(II)chloride (0.1 g, 0.55 mmol) were added. The reaction mixture was stirredat 130° C. for 14 h. After cooling, water and ethyl acetate were addedand the precipitated product was filtered off with suction. The organicphase of the filtrate was removed and the aqueous phase was extractedthree times with ethyl acetate. The combined organic phases were driedover magnesium sulphate and the solvent was removed under reducedpressure. The residue was stirred with dichloromethane and filtered offwith suction. This gave a total of 0.94 g (61% of theory) of6-[2-(5-fluoropyridin-3-yl)-1,3-thiazol-5-yl]pyridine-2-carbonitrile.

HPLC-MS: Log P (HCOOH): 2.51; mass (m/z): 283 (M+H)⁺

¹H NMR (d6-DMSO): 8.02 (d, 1H), 8.20 (t, 1H), 8.32-8.46 (m, 1H), 8.44(d, 1H), 8.75 (d, 1H), 8.84 (s, 1H), 9.12 (s, 1H) ppm

Stage 2: Methyl6-[2-(5-fluoropyridin-3-yl)-1,3-thiazol-5-yl]pyridine-2-carboximidoate

6-[2-(5-Fluoropyridin-3-yl)-1,3-thiazol-5-yl]pyridine-2-carbonitrile(0.33 g, 1.17 mmol) and sodium methoxide (0.13 g, 0.23 mmol) werestirred in methanol (10 ml) and dichloromethane (10 ml) at roomtemperature for 3 d. The precipitated solid was filtered off and thesolvent of the filtrate was removed under reduced pressure. The residuewas dissolved in dichloromethane and filtered through Celite. Thesolvent of the filtrate was removed under reduced pressure. This gave0.32 g (83% of theory) of methyl6-[2-(5-fluoropyridin-3-yl)-1,3-thiazol-5-yl]pyridine-2-carboximidoate.

HPLC-MS: Log P (HCOOH): 0.90; mass (m/z): 315 (M+H)⁺

¹H NMR (d6-DMSO): 4.05 (s, 3H), 7.79-7.81 (m, 2H), 7.87-7.91 (m, 1H),8.05-8.07 (m, 1H), 8.38 (s, 1H), 8.56 (s, 1H), 9.06 (s, 1H), 9.24 (s,1H) ppm

Example K6-[2-(5-Fluoropyridin-3-yl)-1,3-thiazol-5-yl]pyridine-2-carboximideamide hydrochloride (1:1)

Methyl6-[2-(5-fluoropyridin-3-yl)-1,3-thiazol-5-yl]pyridine-2-carboximidoate(0.1 g, 0.32 mmol) and ammonium chloride (0.016 g, 0.3 mmol) werestirred in methanol (3 ml) and dichloromethane (2 ml) at roomtemperature for 2 days. The solvent was removed under reduced pressure,and the residue was taken up in methanol and filtered through Celite.The solvent of the filtrate was removed under reduced pressure, and theresidue was stirred with t-butyl methyl ether and filtered off withsuction. This gave 0.07 g (65% of theory) of6-[2-(5-fluoropyridin-3-yl)-1,3-thiazol-5-yl]pyridine-2-carboximideamide hydrochloride (1:1).

HPLC-MS: Log P (HCOOH): 0.71; mass (m/z): 300 (M+H)⁺

¹H NMR (d6-DMSO): 8.19-8.22 (m, 1H), 8.26-8.31 (m, 2H), 839-8.41 (m,1H), 8.74-8.75 (m, 1H), 8.93 (s, 1H), 9.07-9.08 (m, 1H) ppm

The following compounds of the formula (I) were obtained analogously toor according to the preparation processes described above:

logP Mass Number Compound (HCOOH) NMR data M⁺ + 1  1 (PE A)

1.26 1H NMR (d6-DMSO): 6.82 (d, 1H), 7.45 (d, 1H), 7.59 (dd, 1H), 7.78(t, 1H), 8.30 (m, 2H), 8.57 (dd, 1H), 9.09 (s, 1H), 9.17 (d, 1H), 10.55ppm (s, 1H). 316.0  2 (PE B)

1.86 1H NMR (d6-DMSO): 7.60 (m, 1H), 7.88 (m, 1H), 7.96 (m, 1H), 8.12(m, 1H), 8.30 (m, 1H), 8.70 (m, 1H), 8.89 (m, 1H), 9.10 (m, 1H) ppm.433    3 (PE C)

1.79 1H NMR (d6-DMSO): 3.40 (s, 3H), 8.22 (m, 1H), 8.30 (m, 1H), 8.48(m, 1H), 8.59 (m, 1H), 8.82 (m, 1H), 9.18 (m, 1H), 12.1 (br) ppm 380.1 4 (PE D)

1.98 1H NMR (d6-DMSO): 3.40 (s, 3H), 7.98 (m, 1H), 8.08 (m, 2H), 8.2 (m,1H), 8.58 (m, 1H), 8.70 (m, 1H), 9.08 (m, 1H), 9.40 (m, 1H) ppm. 362.1 5

1.86 1H NMR (d6- DMSO): 2.66 (s, 6H), 7.78- 7.85 (m, 3H), 8.50 (s, 1H),9.17 (s, 1H), 9.26 (s, 1H), 9.40 (s, 2H) 373    6

2.44 1H NMR (d6-DMSO): 1.18 (m, 4H), 3.15 (m, 1H), 8.04 (m, 1H), 8.15(m, 1H), 8.33 (m, 2H), 8.74 (s, 1H), 8.91 (s, 1H), 9.11 (s, 1H), 11.8(br) ppm. 404.9  7

1.63 1H NMR (d6- DMSO): 1.31 (t, 3H), 3.58 (q, 2H), 7.96-7.98 (m, 1H),8.07- 8.14 (m, 2H), 8.83 (s, 1H), 9.20 (s, 1H), 9.38 (s, 2H), 9.52 (s,1H), 11.60 (s, 1H) 358    8

1.48 1H NMR (d6-DMSO): 3.40 (s, 3H), 8.02 (m, 1H), 8.18 (m, 1H), 8.35(m, 1H), 8.95 (s, 1H), 9.30 (s, 1H), 9.40 (s, 2H), 11.8 (br) ppm. 362   9

2.05 1H NMR (d6-DMSO): 3.42 (s, 3H), 8.02 (m, 1H), 8.19 (m, 1H), 8.34(m, 2H), 8.75 (m, 1H), 8.93 (m, 1H), 9.11 (m, 1H), 11.8 (br) ppm. 379  10

1.43 1H NMR (d6-DMSO): 3.21 (s, 3H), 3.78 (t, 2H), 3.92 (m, 2H), 6.79(d, 1H), 7.45 (d, 1H), 7.60 (dd, 1H), 7.78 (t, 1H), 8.29 (m, 2H), 8.58(dd, 1H), 9.10 (s, 1H), 9.16 (d, 1H), 10.67 ppm (br. s, 1H). 360.2 11

1.79 1H NMR (d6-DMSO): 6.75 (m, 1H), 7.50 (m, 1H), 7.93 (m, 2H), 8.12(m, 1H), 8.32 (m, 1H), 8.70 (m, 2H), 9.10 (m, 1H) ppm. 415   12

1.56 1H NMR (d6-DMSO): 3.42 (s, 3H), 7.78 (m, 1H), 8.00 (m, 1H), 8.18(m, 1H), 8.32 (m, 1H), 8.50 (m, 1H), 8.75 (m, 1H), 8.90 (s, 1H), 9.29(m, 1H), 11.8 (br) ppm. 361   13

2.94 1H NMR (d6-DMSO): 7.70 (m, 3H), 7.88 (m, 1H), 8.08 (m, 3H), 8.30(m, 2H), 8.75 (m, 1H), 8.90 (s, 1H), 9.12 (m, 1H), 12.3 (br) ppm. 441  14

2.15 1H NMR (d6-DMSO): 3.74 (s, 6H), 7.59 (dd, 1H), 7.94 (dd, 1H), 8.07(t, 1H), 8.35 (dt, 1H), 8.51 (s, 1H)k, 8.60 (d, 1H), 9.13 (m, 1H), 9.26ppm (d, 1H). 412   15

1.42 1H NMR (d6-DMSO); 6.86 (br. s, 1H), 7.33 (d, 1H), 7.59 (dd, 1H),7.63 (dd, 1H), 7.72 (t, 1H), 7.94 (br. s, 1H), 8.15 (t, 1H), 8.22 (m,1H), 8.31 (br. s, 1H), 8.57 (m, 1H), 8.67 (d, 1H), 8.87 (br. s, 1H),9.09 (d, 1H), 11.34 ppm (br. s, 1H). 379.1 16

2.42 1H NMR (d6- DMSO): 2.65 (s, 6H), 7.76- 7.84 (m, 3H), 8.30- 8.34 (m,1H), 8.45 (s, 1H), 8.57- 8.58 (m, 1H), 9.11 (s, 1H), 9.24 (s, 1H) 390  17

2.4 1H NMR (d6-DMSO): 3.42 (s, 3H), 8.01 (m, 1H), 8.18 (m, 1H), 8.32 (m,2H), 8.78 (s, 1H), 8.92 (m, 1H), 9.18 (s, 1H), 11.8 (br) ppm. 395   18

2.33 1H NMR (d6-DMSO): 1.28 (t, 3H), 3.55 (q, 2H), 7.98 (m, 1H), 8.15(m, 1H), 8.33 (m, 2H), 8.72 (m, 1H), 8.90 (m, 1H), 9.11 (s, 1H), 11.8(br) ppm. 393   19

1.48 1H NMR (d6-DMSO): 1.29 (t, 3H), 3.61 (br. q, 2H), 6.83 (d, 1H),7.44 (d, 1H), 7.61 (m, 1H), 7.77 (t, 1H), 8.29 (m, 1H), 8.58 (m, 1H),9.07 (m, 1H), 9.16 (d, 1H), 10.45 ppm (br. s, 1H). 330.1 20

2.61 1H NMR (d6-DMSO): 1.38 (d, 6H), 3.85 (m, 1H), 7.99 (m, 1H), 8.15(m, 1H), 8.35 (m, 2H), 8.75 (s, 1H), 8.92 (s, 1H), 9.11 (s, 1H), 11.8(br) ppm. 407.1 21

2.97 1H NMR (d6-DMSO): 4.85 (s, 2H), 7.48 (m, 5H), 8.00 (m, 1H), 8.18(m, 1H), 8.33 (m, 2H), 8.72 (s, 1H), 8.89 (s, 1H), 9.10 (s, 1H), 11.8(br) ppm. 455.1 22

1.38 1H NMR (d6- DMSO): 3.44 (s, 3H), 7.98- 8.00 (m, 1H), 8.08- 8.15 (m,2H), 8.84 (s, 1H); 9.20 (s, 1H), 9.38 (s, 2H), 9.54 (s, 1H), 11.75 (s,1H) 344   23

2.24 1H NMR (D6-DMSO): 7.39- 7.42 (m, 3H), 7.74-7.88 (m, 5H), 8.43 (s,1H), 9.15 (s, 1H), 9.19- 9.20 (m, 1H), 9.39 (s, 2H) ppm 406.0 24

1.48 1H NMR (D6-DMSO): 3.43 (s, 3H), 7.61-7.64 (m, 1H), 7.96-7.99 (m,1H), 8.09-8.11 (m, 2H), 8.28-8.31 (m, 1H), 8.58-8.60 (m, 1H), 8.75 (s,1H), 9.17- 9.18 (m, 1H), 9.50 (s1H), 11.70 (s, 1H) ppm 344.0 25

1.77 1H NMR (D6-DMSO): 1.31 (t, 3H), 3.59 (q, 2H), 7.61-7.64 (m, 1H),7.95- 7.97 (m, 1H), 8.09-8.11 (m, 2H), 8.28- 8.32 (m, 1H), 8.56-8.60 (m,1H), 8.76 (s, 1H), 9.17-9.18 (m, 1H), 9.49 (s, 1H), 11.70 (s, 1H) ppm358.1 26

2.21 1H NMR (D6-DMSO): 1.16 (t, 3H), 2.49-2.52 (m, 2H), 7.79-7.89 (m,3H), 8.33-8.36 (m1H), 8.47 (s, 1H), 8.57- 8.58 (m, 1H), 9.11 (s, 1H),9.25 (s, 1H) ppm 376.0 27

1.96 1H NMR (D6-DMSO): 2.95 (s, 6H), 7.61-7.64 (m1H), 7.94-7.97 (m, 1H),8.09-8.10 (m, 1H), 8.59-8.60 (m, 1H), 8.74 (s, 1H), 9.18-9.19 (m, 1H),9.49 (s, 1H), 11.40 (s, 1H) ppm 373.1 28

1.76 1H NMR (D6-DMSO): 1.14- 1.17 (M, 2H); 1.24-1.26 (m, 2H), 3.15- 3.22(m, 1H), 7.98-8.00 (m, 1H), 8.08- 8.15 (m, 2H); 8.83 (s, 1H), 9.20 (s,1H), 9.38 (s, 1H), 9.52 (s, 1H), 11.7 (s, 1H) ppm 371.0 29

2.35 388.0 30

1.85 1H NMR (D6-DMSO): 1,12- 1. l7 (m, 2H), 1.23-1.27 (m, 2H), 7.61-7.64 (m, 1H), 7.95-8.00 (m2H), 8.08- 8.11 (m, 2H), 8.28-8.32 (m, 1H),8.59- 8.60 (m, 1H), 8.75 (s, 1H), 9.17- 9.18 (m, 1H), 9.48 (s, 1H),11.80 (s, 1H) ppm 370.1 31

2.82 1H NMR (D6-DMSO): 7.38- 7.42 (m, 3H), 7.74-7.88 (m, 5H), 8.32- 8.36(m, 1H), 8.39 (s, 1H), 8.56- 8.58 (m, 1H), 9.10 (s, 1H), 9.18 (s, 1H)ppm 424.0 32

2.26 1H NMR (D6-DMSO): 7.42- 7.43 (m, 3H), 7.55-7.59 (m, 1H), 7.76- 7.89(m, 5H), 8.31-8.34 (m, 1H), 8.38 (s, 1H), 8.54-8.56 (m, 1H), 9.14 (s,1H), 9.17-9.18 (m, 1H) ppm 406.0 33

2.89 1H NMR (D6-DMSO): 4.48 (s, 2H), 7.24-7.34 (m, 5H), 7.72-7.90 (m,3H), 8.33-8.36 (m, 1H), 8.46 (s, 1H), 8.57- 8.58 (m, 2H), 9.11 (s, 1H),9.25 (s, 1H) 438.1 34

2.28 1H NMR (D6-DMSO): 4.44 (s2H), 7.24-7.34 (m, 5H), 7.72-7.83 (m, 3H),8.47 (s, 1H), 9.16 (s, 1H), 9.24 (s, 1H), 9.41 (s, 2H) ppm 421.1 35

2.44 1H NMR (D6-DMSO): 4.48 (s, 2H), 7.24-7.34 (m, 5H), 7.57-7.60 (m,1H), 7.73-7.84 (m, 3H), 8.32-8.35 (m, 1H), 8.42 (s, 1H), 8.55-8.57 (m,1H), 9.19- 9.20 (m, 2H) ppm 420.2 36 (PE G)

1.25 1H NMR (D6-DMSO): 3.38 (S, 3H), 7.48-7.49 (m, 1H), 8.32-8.35 (m,1H), 8.45 (s, 1H), 8.56 (s, 1H), 8.59- 8.60 (m, 1H), 9.19-9.20 (m, 1H),9.34 (s, 1H) ppm 350.1 37

1.66 1H NMR (D6-DMSO): 8.33- 8.37 (m, 1H), 8.46 (s, 1H), 8.51 (s, 1H),8.61-8.62 (m, 1H), 9.11 (s, 1H), 9.39 (s, 1H) ppm 368.0 38

2.36 1H NMR (D6-DMSO): 1.15 (t, 6H), 3.44 (q, 4H), 7.94-7.96 (m, 1H),8.06- 8.13 (m, 2H), 8.81 (s, 1H), 9.20 (s, 1H), 9.38 (s, 2H), 8.52 (s,1H) ppm 402.1 39

2.98 1H NMR (D6-DMS0): 1.14 (t, 6H), 3.43 (q, 4H), 7.93-7.95 (m, 1H),8.05- 8.12 (m, 2H), 8.27-8.31 (m, 1H), 8.61- 8.62 (m, 1H), 8.77 (s, 1H),9.10 (s, 1H), 9.50 (s; 1H) ppm 419.1 40

2.49 1H NMR (D6-DMSO): 1.14 (t, 6H), 3.42 (q, 4H), 7.60-7.64 (m, 1H),7.91- 7.93 (m, 1H), 8.05-8.07 (m, 2H), 8.29- 8.32 (m, 1H), 8.58-8.60 (m,1H), 8.71 (s, 1H), 9.18-9.19 (m, 1H), 9.46 (s, 1H) ppm 401.1 41 (PE F)

1.17 1H NMR (D6-DMSO): 2.03 (s, 3H), 7.60-7.64 (m, 1H), 7.92-7.94 (m,1H), 8.08-8.10 (m, 1H), 8.17- 8.20 (m, 1H), 8.29-8.31 (m, 1H), 8.37 (s,1H), 8.59-8.60 (m, 1H), 9.16-9.17 (m, 1H), 9.26 (s, 1H), 12.31 (s, 1H)ppm 344.1 42

1.43 1H NMR (D6-DMSO): 0.92 (t, 3H), 2.32 (q, 2H), 7.60-7.64 (m, 1H),7.92- 7.94 (1H), 8.07-8.09 (m, 1H), 8.17- 8.20 (m, 1H), 8.28-8.31 (m,1H), 8.36 (s, 1H), 8.59-8.60 (m, 1H), 9.16- 9.17 (m, 1H), 9.26 (2H),12.3 (s, 1H) ppm 358.1 43

1.49 1H NMR (D6-DMSO): 0.66- 0.70 (m, 2H), 0.83-0.86 (m, 2H), 1.84 (m,1H), 7.60-7.64 (m, 1H), 7.89- 7.91 (m, 1H), 8.05-8.10 (m, 1H), 8,16-8.19 (m, 1H), 8.29-8.32 (m, 1H), 8.36 (s, 1H), 8.58-8.60 (m, 1H), 9.17-9.18 (m, 1H), 9.28 (s, 1H), 12.6 (br, 1H) ppm 370.1 44

1.55 1H NMR (D6-DMSO): 2.08 (s, 3H), 7.93-7.95 (m, 1H), 8.06-8.08 (m,1H), 8.18-8.22 (m1H), 8.30-8.32 (m, 1H), 8.39 (s, 1H), 8.62-8.63 (m,1H), 9.09 (s, 1H), 9.31 (s, 1H) ppm 362.1 45

1.16 1H NMR (D6-DMSO): 3.20 (S,1H), 7.59-7.62 (m, 1H), 8.26 (s, 1H),8.27- 8.30 (m, 2H), 8.40 (s, 1H), 8.57- 8.58 (m, 1H), 9.13 (s, 1H),9.14- 9.15 (m, 1H) ppm 305.1 46 (PE H)

1.68 1H NMR (D6-DMSO): 2.99, (s, 3H), 7.96 (s, 1H), 8.33 (s, 1H), 8.34(s, 1H), 8.55-8.57 (m, 1H), 9.10 (s, 1H), 9.12 (s, 1H) ppm 368.0 47

1.4 1H NMR (D6-DMSO): 3.65 (s, 1H), 7.92-7.93 (m, 1H), 8.04-8.06 (m,1H), 8.16-8.20 (m, 1H), 8.29-8.33 (m, 1H), 8.35 (s, 1H), 8.63-8.64 (m,1H), 9.09 (s, 1H), 9.28 (s, 1H) ppm 438.1 48

1H NMR (DMSO-d6): 7.60-7.62 (1H, m), 8.24-8.29 (2H, m), 8.38- 8.41 (2H,m), 8.27-8.73 (1H, s), 9.20-9.21 (1H, m) ppm 282   (HCl salt- free) 49

1H NMR (CDCl3) δ: 9.27-9.25 (2H, m), 8.71-8.69 (1H, m), 8.37 (1H, s),8.32-8.29 (1H, m), 7.89- 7.77 (3H, m), 7.45-7.41 (1H, m), 4.04 (3H, s)ppm 50 (PE J)

1H NMR (CDCl3) δ: 9.24 (1H, s), 9.06 (1H, s), 8.56 (1H, s), 8.38 (1H,s), 8.07-8.05 (1H, m), 7.91-7.87 (1H, m), 7.81-7.79 (2H, m), 4.05 (3H,s) ppm 51

1.95 1H NMR (d6-DMS0) = 3.4 (s, 3H), 8.02 (m, 1H), 8.20 (m, 1H), 8.33(m, 1H), 8.95 (m, 2H), 9.15 (m, 1H), 9.48 (m, 1H), 11.80 (br, 1H) ppm.386.0 52

2.275 1H NMR (d6-DMSO) = 3.35 (s, 3H), 3.57 (s, 3H), 7.68 (m, 1H), 8.12(m, 1H), 8.30 (m, 2H), 8.72 (m, 1H), 8.80 (m, 1H), 9.11 (m, 1H) ppm.393.0 53

2.54 1H NMR (d6-DMSO) = 2.95 (s, 6H), 8.00 (m, 1H), 8.17 (m, 1H), 8.35(m, 2H), 8.75 (m, 1H), 8.95 (m, 1H), 9.11 (m, 1H), 11.5 (br, 1H) ppm.408.0 54

3.29 1H NMR (d6-DMSO) = 1.4-1.6 (m, 6H), 3.2-3.4 (m, 4H), 7.99 (m, 1H),8.18 (m, 1H), 8.33 (m, 2H), 8.75 (m, 1H), 8.89 (m, 1H), 9.12 (m, 1H),11.3 (br, 1H) ppm. 448.0 55

2.19 1H NMR (d6-DMSO) = 3.15 (m, 2H), 3.78 (m, 2H), 7.97 (m, 1H), 8.18(m, 1H), 8.33 (m, 2H), 8.72 (m, 1H), 8.90 (m, 1H), 9.10 (m, 1H), 11.7(br, 1H) ppm. 423.1 56

2.77 1H NMR (d6-DMSO) = 1.40 (s, 9H), 7.90 (m, 1H), 8.10 (m, 1H), 8.30(m, 2H), 8.71 (m, 1H), 8.85 (m, 1H), 9.09 (m, 1H), 11.0 (br, 1H) ppm.421.1 57

2.58 1H NMR (d6-DMSO) = 4.71 (m, 2H), 7.99 (m, 1H), 8.15 (m, 1H), 8.33(m, 2H), 8.74 (m, 1H), 8.88 (m, 1H), 9.11 (m, 1H) ppm. 447.0 58

3 1H NMR (d6-DMSO) = 2.69 (s, 6H), 7.90 (m, 1H), 8.05 (m, 1H), 8.25 (m,1H), 8.33 (m, 1H), 8.71 (m, 1H), 8.84 (m, 1H), 9.11 (m, 1H) ppm. 460.059

3.41 1H NMR (d6-DMSO) = 2.55 (s, 3H), 7.91 (m, 1H), 8.05 (m, 1H), 8.25(m, 1H), 8.32 (m, 1H), 8.71 (m, 1H), 8.81 (m, 1H), 9.10 (m, 1H) ppm.495.9 60

3.09 1H NMR (d6-DMSO) = 1.05 (d, 6H), 2.85 (s, 3H), 4.18 (m, 1H), 7.98(m, 1H), 8.17 (m, 1H), 8.32 (m, 2H), 8.72 (m, 1H), 8.90 (m, 1H), 9.11(m, 1H) ppm. 436.0 61

3.47 1H NMR (d6-DMSO) = 0.3-1.2 (m, 8H), 2.99 (s, 3H), 3.30 (m, 1H),7.98 (m, 1H), 8.16 (m, 1H), 8.31 (m, 2H), 8.72 (m, 1H), 8.90 (m, 1H),9.11 (m, 1H) ppm. 462.0 62

1.9 1H NMR (d6-DMSO) = 2.95 (s, 6H), 8.00 (m, 1H), 8.17 (m, 1H), 8.32(m, 1H), 8.95 (m, 1H), 9.30 (m, 1H), 9.40 (m, 1H), 11.4 (m, 1H) ppm.391.0 63 (PE I)

2.04 1H NMR (d6-DMSO) = 2.55 (s, 3H), 3.40 (s, 3H), 4.12 (s, 3H), 7.68(m, 1H), 8.12 (m, 1H), 8.69 (m, 1H), 9.01 (m, 1H) ppm. 396.0 64

1.84 1H NMR (d6-DMSO) = 2.45 (s, 3H), 3.25 (s, 3H), 3.90 (s, 3H), 7.12(m, 1H), 8.29 (m, 1H), 8.72 (m, 1H), 9.04 (m, 1H) ppm. 396.0 65

2.28 1H NMR (d6-DMSO) = 3.71 (s, 3H), 4.98 (s, 2H), 7.70 (m, 1H), 8.17(m, 1H), 8.35 (m, 2H), 8.75 (m, 1H), 8.85 (m, 1H), 9.09 (m, 1H) ppm.418.1 66

2.01 1H NMR (d6-DMSO) = 2.93 (s, 6H), 7.60 (m, 1H), 8.00 (m, 1H), 8.15(m, 1H), 8.32 (m, 1H), 8.40 (m, 1H), 8.73 (m, 1H), 8.90 (m, 1H), 9.23(m, 1H), 11.5 (br, 1H) ppm. 390.0 67

1.72 1H NMR (d6-DMSO) = 2.01 (s, 3H), 8.03 (m, 1H), 8.25 (m, 2H), 8.40(m, 1H), 8.78 (m, 1H), 8.80 (m, 1H), 9.09 (m, 1H), 12.3 (br, 1H) ppm.379.0 68

2.56 1H NMR (d6-DMSO) = 3.65 (s, 3H), 4.71 (s, 2H), 7.70 (m, 1H), 8.12(m, 1H), 8.32 (m, 2H), 8.71 (m, 1H), 8.81 (m, 1H), 9.10 (m, 1H) ppm.417.0 69 (PE E)

1.3 1H NMR (d6-DMSO) = 2.03 (s, 3H), 7.61 (m, 1H), 8.02 (m, 1H), 8.13(m, 1H), 8.30 (m, 1H), 8.41 (m, 1H), 8.71 (m, 1H), 8.91 (m, 1H), 9.20(m, 1H) ppm. 361.0 70

2.07 1H NMR (d6-DMSO) = 1.3 (t, 3H), 3.6 (m, 2H), 8.2 (m, 1H), 8.3 (m,1H) 8.45 (m, 1H), 8.6 (m, 1H), 8.85 (s, 1H) 9.2 (s, 1H) 12 (s, 1H) ppm393.4 71

2.14 1H NMR (d6-DMSO) = 1.15 (m, 2H), 1.25 (m, 1.25), 3.15 (m, 1H), 8.2(m, 1H), 8.3 (m, 1H) 8.45 (m, 1H), 8.6 (m, 1H) 8.85 (s, 1H) 9.2 (s, 1h)12 (s, 1H) ppm 405   72

2.31 1H NMR (d6-DMSO) = 1.35 (d, 6H), 3.8 (m, 1H), 8.2 (m, 1H), 8.3 (m,1H) 8.45 (m, 1H), 8.6 (m, 1H), 8.85 (s, 1H) 9.2 (s, 1H) 12 (s, 1H) ppm407   73

2.42 447   74

1.97 1H NMR (d6-DMSO) = 3.2 (m, 3H), 3.75 (s, 2H), 3.8 (m, 2H) 8.2 (m,1H), 8.3 (m, 1H), 8.5 (m, 1H), 8.6 (m, 1H) 8.85 (s, 1H) 9.2 (s, 1H) 12(s, 1H) ppm 423   75

2.38 447   76

1.43 506   77

2.38 421   78

3.08 482   79 (PE K)

1H NMR (DMSO-D6) δ: 9.08-9.07 (1H, m), 8.93 (1H, s), 8.75-8.74 (1H, m),8.41-8.39 (1H, m), 8.31- 8.26 (2H, m), 8.22-8.19 (1H, m) ppm 300   (HClsalt- free) PE = Preparation Example

The preparation processes described above were used to obtain thefollowing intermediates of the formula (XII):

logP Number Compound (HCOOH) NMR data XII-1

2.4 1H NMR (D6-DMSO): 4.83 (s, 2H), 7.34- 7.40 (m, 5H), 7.94-7.95 (m,1H), 7.98-8.00 (m, 1H), 8.05-8.07 (m, 1H), 12.3 (bs, 1H) XII-2

1.82 1H NMR (D6-DMSO): 2.90 (s, 6H), 7.93- 8.00 (m, 2H), 8.04-8.06 (m,1H), 11.80 (s, 1H) XII-3

1.15 ¹H NMR (d6-DMSO): 3.33 (s, 3H), 7.78 (m, 1H), 8.05 (m, 2H) ppm.XII-4

1.28 ¹H NMR (d6-DMSO): 3.37 (s, 3H), 7.95 (m, 2H), 8.06 (m, 1H) ppm.XII-5

1.54 1H NMR (D6-DMSO): 1.27 (t, 3H), 3.50 (q, 2H), 7.94-8.01 (m, 2H),8.05- 8.07 (m, 1H), 11.90 (s, 1H) XII-6

2.32 1H NMR (DMSO): 7.57-7.70 (m, 3H), 7.84-8.01 (m, 5H) XII-7

1.7 1H NMR (D6-DMSO): 1.07-1.21 (m, 4H), 3.05-3.11 (m, 1H), 7.93-8.01(m, 3H), 8.06- 8.08 (m, 2H), 12.00 (s, 1H)

The preparation processes described above were used to obtain thefollowing intermediates of the formula (XIII):

logP Number Compound (HCOOH) NMR data XIII-1

1.51 1H NMR (DMSO): 7.93 (m, 1H), 8.03 (m, 1H), 8.17 (m, 1H), 8.63 (m,1H), 9.02 (m, 1H) XIII-2

1.94 1H NMR (DMSO): 7.96 (m, 1H), 8.05 (m, 1H), 8.42 (m, 1H), 8.73 (m,1H), 9.11 (m, 1H) XIII-3

0.69 1H NMR (DMSO): 7.95 (m, 1H), 8.07 (m, 1H), 9.25 (m, 1H), 9.30 (m,2H) XIII-4

1.34 1H NMR (DMSO): 8.00 (m, 1H), 8.08 (m, 1H), 8.83 (m, 1H) 9.12 (m,1H), 9.40 (m, 1)

The preparation processes described above were used to obtain thefollowing intermediates of the formula (XIV):

logP Number Compound (HCOOH) NMR data XIV-1

1.32 1H NMR (d6-DMSO): 0.92 (t, 3H), 2.28 (q, 2H), 7.99 (m, 1H),8.06-8.13 (m, 2H), 12.39 (br, 1H) XIV-2

0.95 1H NMR (d6-DMSO): 1.98 (s, 3H), 7.98-8.12 (m, 3H), 12.4 (br, 1H)ppm

The preparation processes described above were used to obtain thefollowing intermediates of the formula (XV):

logP Number Compound (HCOOH) NMR data XV-1

0.82 1H NMR (d6- DMSO): 3.33 (s, 3H), 8.61 (s, 1H), 12.00 (s, 1H)

The preparation processes described above were used to obtain thefollowing intermediates of the formula (XVI):

logP Number Compound (HCOOH) NMR data XVI-1

0.63 1H NMR (d6- DMSO): 3.31 (s, 3H), 8.31 (s, 1H)

The preparation processes described above were used to obtain thefollowing intermediates of the formula (XVII):

logP Number Compound (HCOOH) NMR data XVII-1

0.99 1H NMR (d6-DMSO): 7.43 (s, 2H), 7.60- 7.63 (m, 1H), 7.76 (d, 1H),8.00 (d, 1H), 8.11 (t, 1H), 8.28-8.31 (m, 1H), 8.53 (s, 1H), 8.58- 8.60(m, 1H), 9.16-9.17 (m, 1H), 9.33 (s, 1H) XVII-2

1.44 1H NMR (d6-DMSO): 7.78 (s, 2H), 7.77- 7.79 (m, 1H), 7.99-8.01 (m,1H), 8.12- 8.14 (m, 1H), 8.29-8.32 (m, 1H), 8.57 (s, 1H), 8.62-8.63 (m,1H), 9.09 (s, 1H), 9.41 (s, 1H) XVII-3

0.89 1H NMR (d6-DMSO): 7.48 (s, 2H), 7.78- 7.80 (m, 1H), 7.99-7.80 (m,1H), 8.12- 8.16 (m, 1H), 8.60 (s, 1H), 9.21(s, 1H), 9.38 (s, 2H), 9.41(s, 1H)

1) Description of Method for Determination of the log P Values (FormicAid Method)

The log P values given in the table were determined in accordance withEEC Directive 79/831 Annex V.A8 by HPLC (High Performance LiquidChromatography) using a reverse-phase column (C 18). Temperature: 55° C.

Eluents for determination in the acidic range (pH 3.4):

Eluent A: acetonitrile+1 ml of formic acid/litre. Eluent B: water+0.9 mlof formic acid/litre.

Gradient: from 10% eluent A/90% eluent B to 95% eluent A/5% eluent B in4.25 min.

The calibration was effected with unbranched alkan-2-ones (having 3 to16 carbon atoms) with known log P values (log P values determined on thebasis of the retention times by linear interpolation between twosuccessive alkanones). The lambda max values were determined in themaxima of the chromatographic signals using the UV spectra from 200 nmto 400 nm.

21 Measurement of the NMR Spectra

The NMR spectra were determined with a Bruker Avance 400 fitted with aflow probe head (volume 60 μl). The solvent used was CD₃CN or d₆-DMSO,with tetramethylsilane (0.00 ppm) used as a reference. In particularcases, the NMR spectra were determined with a Bruker Avance II 600. Thesolvent used was CD₃CN or d₆-DMSO, with tetramethylsilane (0.00 ppm)used as a reference.

The splitting of the signals was described as follows: s (singlet), d(doublet), t (triplet), q (quartet), quin (quintet), m (multiplet).

Biological Examples Myzus Test (Spray Treatment)

Solvent 78 parts by weight of acetone

-   -   1.5 parts by weight of dimethylformamide

Emulsifier: 0.5 part by weight of alkylaryl polyglycol ether

To prepare an appropriate active ingredient preparation, 1 part byweight of active ingredient is mixed with the stated amounts of solventand emulsifier, and the concentrate is diluted withemulsifier-containing water to the desired concentration.

Discs of Chinese cabbage (Brassica pekinensis) infested by all stages ofthe green peach aphid (Myzus persicae) are sprayed with an activeingredient preparation of the desired concentration.

After the desired time, the efficacy in % is determined. 100% means thatall of the aphids have been killed; 0% means that none of the aphidshave been killed.

In this test, for example, the following compounds of the PreparationExamples showed, at an application rate of 500 g/ha, an efficacy of 80%:1, 10, 15, 21, 28, 62, 63

In this test, for example, the following compounds of the PreparationExamples showed, at an application rate of 500 g/ha, an efficacy of 90%:5, 14, 23, 32, 34, 37, 38, 45, 47, 48, 65, 74

In this test, for example, the following compounds of the PreparationExamples showed, at an application rate of 500 g/ha, an efficacy of100%: 2, 3, 4, 6, 7, 8, 9, 11, 12, 13, 16, 17, 18, 19, 20, 22, 24, 25,26, 27, 29, 30, 31, 33, 35, 36, 39, 40, 41, 42, 43, 44, 46, 51, 52, 53,54, 55, 56, 57, 58, 59, 60, 61, 64, 66, 67, 68, 69, 70, 71, 72, 73, 75,76, 77, 78.

Tetranychus Test, OP-Resistant (Spray Treatment)

Solvent: 78.0 parts by weight of acetone

-   -   1.5 parts by weight of dimethylformamide

Emulsifier: 0.5 part by weight of alkylaryl polyglycol ether

To prepare an appropriate active ingredient preparation, 1 part byweight of active ingredient is mixed with the stated amounts of solventand emulsifier, and the concentrate is diluted withemulsifier-containing water to the desired concentration. Discs of beanleaves (Phaseolus vulgaris) infested by all stages of the red spidermite (Tetranychus urticae) are sprayed with an active ingredientpreparation of the desired concentration.

After the desired time, the efficacy in % is determined. 100% means thatall of the spider mites have been killed; 0% means that none of thespider mites have been killed.

In this test, for example, the following compound of the PreparationExamples showed, at an application rate of 500 g/ha, an efficacy of100%: 5.

Meloidogyne Incognita Test

Solvent: 80.0 parts by weight of acetone

To prepare an appropriate active ingredient preparation, 1 part byweight of active ingredient is mixed with the stated amounts of solvent,and the concentrate is diluted with water to the desired concentration.

Vessels are filled with sand, active ingredient solution, Meloidogyneincognita egg/larvae suspension and lettuce seeds. The lettuce seedsgerminate and the plants develop. Galls develop on the roots.

After the desired time, the nematicidal action is determined by the gallformation in %. 100% means that no galls were found; 0% means that thenumber of galls on the treated plants corresponds to the untreatedcontrol.

In this test, for example, the following compounds of the preparationexamples showed, at an application rate of 20 ppm, an efficacy of 100%:56, 70, 75, 78.

Myzus Spray Test

Preliminary mixture solvent: Sorpol® SD: Sorpol® BDB:dimethylformamide=3:3:14

To prepare an appropriate active ingredient preparation, 10 mg of activeingredient are mixed with 0.05 ml of solvent and the concentrate isdiluted with water to the desired concentration. The solution in eachcase contains 1000 ppm of RME (rapeseed oil methyl ester) and AMS(ammonium sulphate).

Aubergine plants (Solanum melongena var. Senryo 2gou) infested by allstages of the green peach aphid (Myzus persicaeorganophosphate/carbamate resistant strain) are sprayed with an activeingredient preparation of the desired concentration.

After 6 days, the efficacy in % is determined:

100%: all insects killed,98%: 1-4 insects survive,95%: 5-20 insects survive,60%: fewer insects survive than in the untreated control and0%: no difference from the untreated control.

In this test, for example, the following compounds of the preparationexamples showed, at an application rate of 100 ppm, an efficacy of 100%:49, 50.

1. Compounds of the formula (I)

in which A¹ and A² are each independently hydrogen, halogen, cyano,nitro, alkyl, cycloalkyl or alkoxy, G¹ is N or C-A¹ and G² is a radicalfrom the group of

in which the arrow in each case marks the bond to the adjacent ring, R¹in the case of the heterocycles (A) and (D) is hydrogen, halogen, cyano,alkyl, alkoxy, amino, alkylamino, dialkylamino, alkylthio or haloalkyland R¹ in the case of heterocycle (C) is hydrogen, alkyl or haloalkyl, Bis hydrogen, halogen, cyano, nitro, alkyl, cycloalkyl, haloalkyl, amino,alkylamino, dialkylamino, alkylthio or alkoxy and G³ is optionallysubstituted heterocyclyl, optionally substituted heteroaryl oroptionally substituted aryl and G⁴ is a radical from the group of

and in the case of the heterocycles (A), (B) and (C) is also the radical

in which the arrow in each case marks the bond to G³, X is oxygen orsulphur, n is 1 or 2, R² is a radical from the group of hydrogen, alkyl,haloalkyl, cyanoalkyl, alkoxy, haloalkoxy, alkenyl, alkynyl andalkoxyalkyl, in each case optionally halogen-substituted alkylcarbonyland alkylsulphonyl, in each case optionally halogen-substitutedalkoxycarbonyl, in each case optionally halogen-, alkyl-, alkoxy-,haloalkyl- and cyano-substituted cycloalkylcarbonyl, or a cation, forexample a mono- or divalent metal ion or an optionally alkyl- orarylalkyl-substituted ammonium ion, R³ and R⁷ are each independently aradical from the group of in each case optionally substituted alkyl,alkenyl and alkynyl, in each case optionally substituted cycloalkyl,cycloalkylalkyl and cycloalkenyl, in which the rings may contain atleast one heteroatom from the group of sulphur, oxygen (where oxygenatoms must not be immediately adjacent) and nitrogen, in each caseoptionally substituted aryl, heteroaryl, arylalkyl and heteroarylalkyland an optionally substituted amino group, R² and R³ may also form,together with the N—S(O)_(n) group to which they are bonded, a saturatedor unsaturated and optionally substituted 4- to 8-membered ring whichmay contain one or more further heteroatoms from the group of sulphur,oxygen (where oxygen atoms must not be immediately adjacent) andnitrogen and/or at least one carbonyl group, R⁵ is a radical from thegroup of in each case optionally substituted alkyl, alkoxy, alkenyl andalkynyl, in each case optionally substituted cycloalkyl, cycloalkylalkyland cycloalkenyl, in which the rings may contain at least one heteroatomfrom the group of sulphur, oxygen (where oxygen atoms must not beimmediately adjacent) and nitrogen, in each case optionally substitutedaryl, heteroaryl, arylalkyl and heteroarylalkyl and an optionallysubstituted amino group, R⁸ is a radical from the group of hydrogen, ineach case optionally substituted alkyl, alkoxy, alkenyl and alkynyl, ineach case optionally substituted cycloalkyl, cycloalkylalkyl andcycloalkenyl, in which the rings may contain at least one heteroatomfrom the group of sulphur, oxygen (where oxygen atoms must not beimmediately adjacent) and nitrogen, in each case optionally substitutedaryl, heteroaryl, arylalkyl and heteroarylalkyl and an optionallysubstituted amino group, R² and R⁵ may also form, together with theN—C(X) group to which they are bonded, a saturated or unsaturated andoptionally substituted 4- to 8-membered ring which may contain one ormore further heteroatoms from the group of sulphur, oxygen (where oxygenatoms must not be immediately adjacent) and nitrogen and/or at least onecarbonyl group, R⁶ is hydrogen or alkyl, R² and R⁶ may also form,together with the nitrogen atoms to which they are bonded, a saturatedor unsaturated and optionally substituted 4- to 8-membered ring whichmay contain at least one further heteroatom from the group of sulphur,oxygen (where oxygen atoms must not be immediately adjacent) andnitrogen and/or at least one carbonyl group, R² and R⁷ in the radical(E) may also form, together with the N—S(O)_(n) group to which they arebonded, a saturated or unsaturated and optionally substituted 4- to8-membered ring which may contain one or more further heteroatoms fromthe group of sulphur, oxygen (where oxygen atoms must not be immediatelyadjacent) and nitrogen and/or at least one carbonyl group, R⁶ and R⁷ mayalso form, together with the N—S(O)_(n) group to which they are bonded,a saturated or unsaturated and optionally substituted 4- to 8-memberedring which may contain one or more further heteroatoms from the group ofsulphur, oxygen (where oxygen atoms must not be immediately adjacent)and nitrogen and/or at least one carbonyl group, R² and R⁸ may alsoform, together with the nitrogen atom to which they are bonded, asaturated or unsaturated and optionally substituted 4- to 8-memberedring which may contain one or more further heteroatoms from the group ofsulphur, oxygen (where oxygen atoms must not be immediately adjacent)and nitrogen and/or at least one carbonyl group, L is oxygen or sulphur,R⁹ and R¹⁰ are each independently an in each case optionally substitutedradical from the group of alkyl, alkenyl, alkynyl, alkoxy, alkenyloxy,alkynyloxy, cycloalkyl, cycloalkyloxy, cycloalkenyloxy,cycloalkylalkoxy, alkylthio, alkenylthio, phenoxy, phenylthio,benzyloxy, benzylthio, heteroaryloxy, heteroarylthio, heteroarylalkoxyand heteroarylalkylthio, R⁹ and R¹⁰ may also form, together with thephosphorus atom to which they are bonded, a saturated or unsaturated andoptionally substituted 5- to 7-membered ring which may contain one ortwo heteroatoms from the group of oxygen (where oxygen atoms must not beimmediately adjacent) and sulphur, R¹¹ and R¹² are each independently anin each case optionally substituted radical from the group of alkyl,alkenyl, alkynyl, phenyl and phenylalkyl, Y¹ and Y² are eachindependently C═O or S(O)₂, m is 1, 2, 3 or 4, R¹³ is a radical from thegroup of hydrogen, alkyl, haloalkyl, cyano, cyanoalkyl, hydroxyalkyl,hydroxyl, alkoxy, alkoxyalkyl, alkylthioalkyl, alkenyl, haloalkenyl,cyanoalkenyl, alkynyl, haloalkynyl, cyanoalkynyl, alkylcarbonyl andalkoxycarbonyl, Y³ is a radical from the group of alkoxy, haloalkoxy,alkylthio, haloalkylthio and NR¹⁴R¹⁵ where R¹⁴ and R¹⁵ are eachindependently radicals from the group of hydrogen, alkyl, cycloalkyl,cycloalkylalkyl, haloalkyl, cyano, cyanoalkyl, hydroxyl, alkoxy,haloalkoxy, hydroxyalkyl, alkoxyalkyl, alkylthioalkyl, alkenyl,haloalkenyl, cyanoalkenyl, alkynyl, haloalkynyl, cyanoalkynyl,alkylcarbonyl and alkoxycarbonyl, or R¹⁴ and R¹⁵ together with thenitrogen atom to which they are bonded may form an optionallysubstituted saturated or unsaturated 5- to 8-membered ring optionallycontaining heteroatoms, G³ and G⁴ may additionally also together form anoptionally substituted heterocycle which optionally contains one or morefurther heteroatoms from the group of oxygen, nitrogen and sulphur, andsalts and N-oxides of the compounds of the formula (I).
 2. Compounds ofthe formula (IA)

in which G¹ is C—H, C—F, C—Cl or N, R¹ is hydrogen or methyl and G⁴ isone of the (E), (L) and (N) radicals specified in claim
 1. 3. Compoundsof the formula (IB)

in which G¹ is C—H, C—F, C—Cl or N and G⁴ is one of the (E), (L) and (N)radicals specified in claim
 1. 4. Compounds of the formula (IC)

in which G¹ is C—H, C—F, C—Cl or N, R¹ is hydrogen or methyl, B ishydrogen and G⁴ is one of the (E), (L) and (N) radicals specified inclaim
 1. 5. Compounds of the formula (ID)

in which G¹ is C—H, C—F, C—Cl or N, R¹ is hydrogen or methyl, B ishydrogen and G⁴ is one of the (E) and (L) radicals specified in claim 1.6. Composition characterized by a content of at least one compound ofthe formula (I) according to claims 1 to
 5. 7. Method for controllingpests, characterized in that a compound of the formula (I) according toclaims 1 to 5 or a composition according to claim 6 is allowed to act onthe pests and/or their habitat.
 8. Compounds of the formula (XII)

in which R¹⁶ is fluorine, chlorine, bromine or iodine and X, R² and R⁷are each as defined in claim
 1. 9. Compounds of the formula (XIII)

in which G¹ is nitrogen, C-halogen, C-cyano, C-nitro, C-alkyl,C-cycloalkyl or C-alkoxy.
 10. Compounds of the formula (XIV)

in which R¹⁶ is fluorine, chlorine, bromine or iodine and X, R² and R⁵are each as defined in claim
 1. 11. Compounds of the formula (XV)

in which R¹⁶ is fluorine, chlorine, bromine or iodine and X, R² and R⁷are each as defined in claim
 1. 12. Compounds of the formula (XVI)

in which R¹⁶ is fluorine, chlorine, bromine or iodine and X, R² and R⁷are each as defined in claim
 1. 13. Compounds of the formula (XVII)

in which G¹ is nitrogen, C-halogen, C-cyano, C-nitro, C-alkyl,C-cycloalkyl or C-alkoxy, and R² is as defined in claim
 1. 14. Compoundsof the formula (XVIII)

in which G¹ is nitrogen, C-halogen, C-cyano, C-nitro, C-alkyl,C-cycloalkyl or C-alkoxy, and R² is as defined in claim 1.